Category: 76632-23-0

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Synthesis of Dimethyl Sulfomycinamate, published in 2003-11-13, which mentions a compound: 76632-23-0, Name is (2-Methylthiazol-4-yl)methanol, Molecular C5H7NOS, Recommanded Product: 76632-23-0.

Di-Me sulfomycinamate I, generated in the methanolysis of the thiopeptide antibiotic sulfomycin I, is prepared in 13 steps and 8% overall yield via Bohlmann-Rahtz heteroannulation of 1-(oxazol-4-yl)enamine II and α-keto ester Me3SiCCCOCO2Me.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

COA of Formula: C5H7NOS. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: (2-Methylthiazol-4-yl)methanol, is researched, Molecular C5H7NOS, CAS is 76632-23-0, about Total Syntheses of Epothilones B and D. Author is Jung, Jae-Chul; Kache, Rajashaker; Vines, Kimberly K.; Zheng, Yan-Song; Bijoy, Panicker; Valluri, Muralikrishna; Avery, Mitchell A..

A convergent, total synthesis of epothilones B (I; X = O) and D (I; X = bond) is described. The key steps are Normant coupling to establish the desired (Z)-stereochem. at C12-C13, Wadsworth-Emmons olefination, diastereoselective aldol condensation of aldehyde II with the enolate of keto acid derivatives to form the C6-C7 bond, selective deprotection, and macrolactonization.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《p-Mentha-1,5,8(9)-triene and its pyrolysis to dehydroocimene》. Authors are Alder, Kurt; Schumacher, Marianne.The article about the compound:(2-Methylthiazol-4-yl)methanolcas:76632-23-0,SMILESS:OCC1=CSC(C)=N1).Application of 76632-23-0. Through the article, more information about this compound (cas:76632-23-0) is conveyed.

LiAlH4 reduction of d(+)-carvone (I) gives 90% d-cis-carveol (II) which is dehydrated to p-mentha-1,5,8(9)-triene (III) whose structure is established, and which, on pyrolysis, gives 2,6-dimethyl-1,3,5,7-octatetraene (IV), called dehydroocimene. I (90 g.) in about 150 cc. ether added dropwise to 7.5 g. LiAlH4 in ether, warmed 1 hr., extracted with H2O then dilute H2SO4, and the ether layer evaporated and distilled gives carveol, b13 111-12°, which, distilled over KHSO4 in vacuo to 100° to remove volatile matter, leaves a residue which fractionated gives 60-5 g. III, b14 65-6.5°, nD20 1.4883, d20 0.8656, MR 44.69, λ 262 mμ (log ε 3.481). Ozonization of III in EtOAc gives CH2O in good yield. III with H and PtO2 takes up 6 H atoms/mole to give p-menthane, or warmed with 5% HCl in AcOH gives a quant. yield of p-cymene. III (6.5 g.) heated 15 hrs. in bomb with over 2 moles/mole III of di-Me acetylenedicarboxylate in 10 cc. PhMe at 140°, the product b0.04 90-120°, saponified and recrystallized from EtOAc gives the insoluble 3,6-dihydro-4-methyl-o-phthalic acid, m. 216°, and the soluble 4-methyl-o-phthalic acid, m. 159°, in equal amounts III adds to maleic anhydride in ether to give the adduct (V), m. 89-90°, whose hydrogenated derivative (VI), m. 91-2°, does not give CH2O on ozonization. V with 50% H2SO4 in dioxane 2-3 days gives a solution which extracted with ether gives the monolactone (VII), m. 184-5°; Me ester (VIII), m. 128-9°. Ozonization of VII in EtOAc gives acetone and an oxo acid, m. 215°; Me ester, m. 168°. VIII boiled with 10% NaOEt and the chief product lactonized with 50% H2SO4 in dioxane gives the dilactone (IX), m. 158°. The di-Me ester of V with 10% NaOEt gives a trans acid, m. 256°, whose dilactone, m. 164-5°, is not identical with IX. III (8 g.) refluxed 6-7 hrs. with 7 g. α-naphthoquinone in 15 cc. C6H6, the C6H6 removed, and the residue extracted with MeOH gives 80-90% adduct (X), m. 90-1°. Aeration of X in hot MeOH and alc. KOH gives an oil which boiled with EtOH gives 2-methylanthraquinone, m. 174-5°, and isoprene. Pyrolysis of III (105 g.) by distilling it at 12 mm. through a 75-cm. quartz tube at 520-40° at such a rate as to give one drop cracking product/sec. gives a hydrocarbon mixture which, redistilled in an N atm. at 36-72°/13 mm., gives mostly IV, nD20 1.4959, d20 0.8671, λ 303 mμ (log ε 3.934). IV is easily cyclized to p-cymene by distillation or by treatment with iodine in C6H6. IV (80 g.) in 100 cc. ether under N treated with 50 g. maleic anhydride 12 hrs. at room temperature, the unreacted IV removed by distillation, the residue taken up in Na2CO3 solution, extracted with ether, and acidified gives the ether-soluble adduct (XI), m. 191°. Ozonization of XI gives acetaldehyde while dehydrogenation of 2.5 g. XI with 0.8 g. S at 200° followed by extraction with Na2CO3 solution and acidification give 4,7-dimethylnaphthalene-1,2-dicarboxylic acid (XII), m. 213-14°; anhydride, m. 235-6°. Oxidation of 0.5 g. XII with 3 cc. HNO3 (d. 1.4) 16 hrs. at 140° in bomb followed by reaction with CH2N2 gives C6H(CO2Me)5, m. 147-8°. XI (1.2 g.) in CHCl3 with Br gives HBr and needles of C14H16O4Br2, m. 233°. Catalytic hydrogenation of XI in AcOH adds 1 mole H to give C14H20O4, m. 177-8°, which can be dehydrogenated by S to XII. Oxidation of XI by alk. KMnO4 gives a product of unknown constitution, C14H18O7, m. 282° (decomposition). IV (8 g.) refluxed 5-6 hrs. in C6H6 with 7 g. α-naphthoquinone, the C6H6 removed, and the residue recrystallized from MeOH gives a nearly quant. yield of adduct (XIII), needles, m. 115-16°. Dehydrogenation of XIII by air in 17% alc. KOH gives yellow needles of C20H16O2 (XIV), m. 145-6°. XIV is oxidized by HNO3 at 200° to give an acid which with CH2N2 gives tri-Me anthraquinone-1,2,3-tricarboxylate, m. 184-5°. Dehydrogenation of XIV by S at 190° gives 2′,3-dimethyl-1,2-benzanthraquinone (XV), m. 205°. XV is reduced by Zn and acetylated to C24H20O4, m. 175-6°, which is again oxidized by air in alc. KOH to XV. Addition of IV to di-Me acetylenedicarboxylate in C6H6, warming 3-4 hrs., and distilling give an ester, C16H18O4, m. 118-19°, whose saponification with alc. KOH gives an acid, m. 213-14°, which heated gives the anhydride, m. 197-8°, and which dehydrogenated with S and then boiled with acetic anhydrous gives 4,7-dimethylnaphthalene-1,2-dicarboxylic anhydride, m. 235-6°.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Youji Huaxue called Synthesis (2E)-2-methyl-3-(2-methyl-4-thiazolyl)-2-propenethioic acid S-[2-(acetylamino)ethyl] ester and 2-methyl-4-thiazolecarbothioic acid S-[2-(acetylamino)ethyl] (modified intermediates for epothilone biosynthesis), Author is Sun, He; Hu, Wei; Wang, Zong-Heng; Li, Yue-Zhong; Zhao, Gui-Long; Wang, Jian-Wu, which mentions a compound: 76632-23-0, SMILESS is OCC1=CSC(C)=N1, Molecular C5H7NOS, Safety of (2-Methylthiazol-4-yl)methanol.

Methods for the synthesis of the title compounds [i.e., (2-methyl-4-thiazolyl)carboxylic [2-(acetamido)ethyl]thiol thioester and (E)-2-methyl-3-(2-methyl-4-thiazolyl)acrylic [2-(acetamido)ethyl]thiol thioester] are reported here. In order to investigate the biosynthesis of epothilones and generate novel biosynthetic epothilone analogs by a precursor-directed biosynthesis, two modified intermediates for epothilone biosynthesis were designed and synthesized. The new synthetic procedures utilized are inexpensive and convenient. The structures of these compounds were confirmed by IR, MS, 1H NMR and 13C NMR spectra and elemental anal.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Computed Properties of C5H7NOS. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: (2-Methylthiazol-4-yl)methanol, is researched, Molecular C5H7NOS, CAS is 76632-23-0, about Design, synthesis, and biological testing of potential heme-coordinating nitric oxide synthase inhibitors. Author is Litzinger, Elizabeth A.; Martasek, Pavel; Roman, Linda J.; Silverman, Richard B..

Based on computer modeling of the active site of nitric oxide synthases (NOS), a series of 10 amidine compounds was designed including potential inhibitors that involve the coordination of side-chain functional groups with the iron of the heme cofactor. The most potent and selective compound was the methylthio amidine analog (H-Orn(C(:NH)CH2SMe)-OH), which was more potent than L-nitroarginine with 185-fold selectivity for inhibition of neuronal NOS over endothelial NOS. It also exhibited time-dependent inhibition, but did not involve the mechanism previously proposed for other amidine inhibitors of NOS. None of the compounds, however, exhibited heme-binding characteristics according to absorption spectroscopy.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Nicolaou, K. C.; Rhoades, Derek; Wang, Yanping; Bai, Ruoli; Hamel, Ernest; Aujay, Monette; Sandoval, Joseph; Gavrilyuk, Julia researched the compound: (2-Methylthiazol-4-yl)methanol( cas:76632-23-0 ).Recommanded Product: (2-Methylthiazol-4-yl)methanol.They published the article 《12,13-Aziridinyl Epothilones. Stereoselective Synthesis of Trisubstituted Olefinic Bonds from Methyl Ketones and Heteroaromatic Phosphonates and Design, Synthesis, and Biological Evaluation of Potent Antitumor Agents》 about this compound( cas:76632-23-0 ) in Journal of the American Chemical Society. Keywords: epothilone aziridinyl stereoselective preparation antitumor. We’ll tell you more about this compound (cas:76632-23-0).

The synthesis and biol. evaluation of a series of 12,13-aziridinyl epothilone B analogs is described. These compounds were accessed by a practical, general process that involved a 12,13-olefinic Me ketone as a starting material obtained by ozonolytic cleavage of epothilone B followed by tungsten-induced deoxygenation of the epoxide moiety. The attachment of the aziridine structural motif was achieved by application of the Ess-Kurti-Falck aziridination, while the heterocyclic side chains were introduced via stereoselective phosphonate-based olefinations. In order to ensure high (E) selectivities for the latter reaction for electron-rich heterocycles, it became necessary to develop and apply an unprecedented modification of the venerable Horner-Wadsworth-Emmons reaction, employing 2-fluoroethoxyphosphonates that may prove to be of general value in organic synthesis. These studies resulted in the discovery of some of the most potent epothilones reported to date. Equipped with functional groups to accommodate modern drug delivery technologies, some of these compounds exhibited picomolar potencies that qualify them as payloads for antibody drug conjugates (ADCs), while a number of them revealed impressive activities against drug resistant human cancer cells, making them desirable for potential medical applications.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of thiazole derivatives. XVII. Hydroxymethyl- substituted 2-methylthiazoles》. Authors are Zubarovskii, V. M.; Moskaleva, R. N..The article about the compound:(2-Methylthiazol-4-yl)methanolcas:76632-23-0,SMILESS:OCC1=CSC(C)=N1).Quality Control of (2-Methylthiazol-4-yl)methanol. Through the article, more information about this compound (cas:76632-23-0) is conveyed.

cf. CA 55,514b; 56, 15495i. Et 2-methylthiazole-4-carboxylate and LiAlH4, in Et2O gave 66-9% 2-methyl-4-(hydroxymethyl)thiazole (I), b5 104°, which solidified on cooling; methiodide m. 208°; Me p-totuenesulfonate (from Ag p-toluenesulfonate and the methiodide) m. 128°; Et p-toluenesulfonate, m.p. unstated. Similarly was prepared 63-5% 2-methyl-5-(hydroxymethyl)thiazole (II), b3 117.5°; methiodide m. 186°; ethiodide m. 136-7°. I and Ac2O refluxed 4 hrs. gave I acetate, b10 111°; II acetate b7 104°. I and PCl5 in MePh 15 min. at 110° gave, after an aqueous treatment and neutralization, 63.2% 2-methyl-4-(chloromethyl)thiazole, b10 84°, a mild eye irritant. Similarly was prepared 2-methyl-5-(chloromethyl)thiazole, b13 93.5° (91%). The chloromethyl derivatives and EtONa in EtOH gave: 2-methyl-4-(ethoxymethyl)thiazole, b13 93.5° (Et p-toluenesulfonate, 94%, undescribed); 2-methyl-5-(ethoxymethyl)thiazole, 65.5%, b7 73° (Et p-toluenesulfonate, 85%, undescribed). Condensation of these thiazoles with the usual components of cyanine dye intermediates (p-Me2NC6H4CHO, 2-(methylthio)benzothiazole Et tosylate, HC(OEt)3, 2-(anilinovinyl)-5-methoxybenzothiazole Et tosylate, and 2-(acetanilidovinyl)benzothiazole Et tosylate) gave the following dyes: [3-methyl-5-(hydroxymethyl)-2-thiazole](3-ethyl-2-benzothiazole)cyanine iodide, 21%, decompose 256°, λmaximum 414 mμ; [3-methyl-5-(hydroxymethyl)-2-thiazole](3-ethyl-2- benzothiazole)cyanine iodide, 16%, decompose 296°, λmaximum 417 mμ; 3,3′-diethyl-4,4′-bis(hydroxymethyl)thiazolocarbocyanine perchlorate, 12%, decompose 183°, λmaximum 553 mμ; 3,3′-diethyl-5,5′-bis(hydroxymethyl)thiazolocarbocyanine perchlorate, 13%, decompose 191°, λmaximum 555 mμ; [3-methyl-4-(hydroxymethyl)-2-thiazole] (3-ethyl-5-methoxy-2-benzothiazole)trimethinecyanine perchlorate, 87%, m. 167°, λmaximum 560 mμ; [3-methyl-5-(hydroxymethyl)-2-thiazole] [3-ethyl-5-(methoxymethyl)-2-benzothiazole]-trimethinecyanine perchlorate, 85%, m. 176°, λmaximum 567 mμ; [3-methyl-4-(hydroxymethyl)-2-thiazole] (3-ethyl-4,5-benzo-2-benzothiazole)trimethinecyanine perchlorate, 52%, decompose 236°, λmaximum 568 mμ; [3-methyl-5-(hydroxymethyl)-2-thiazole] (3-ethyl-4,5-benzo-2-benzothiazole)trimethinecyanine perchlorate, 42%, decompose 241°, λmaximum 571 mμ; 2-(p-dimethylaminostyryl)-4-(hydroxymethyl)thiazole Me tosylate, 54%, decompose 297°, λmaximum 485 mμ; 2-(p-dimethylaminostyryl)-4-(ethoxymethyl)thiazole Et perchlorate, 60%, m. 168°, λmaximum 491 mμ; 2-(p-dimethylaminostyryl)-4-(acetoxymethyl)thiazole Et perchlorate, 40%, m. 193°, λmaximum 496 mμ; 2-(p-dimethylaminostyryl)-5-(hydroxymethyl)thiazole Me tosylate, 90%, m. 212°, λmaximum 489 mμ; 2-(p-dimethylaminostyryl)-5-(ethoxymethyl)thiazole Et perchlorate, 18%, m. 167°, λmaximum 492 mμ; and 2-(p-dimethylaminostyryl)-5-(acetoxymethyl)thiazole Et perchlorate, 42%, m. 195° λmaximum 500 mμ.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Chemical Communications (Cambridge, United Kingdom) called First synthesis of an amythiamicin pyridine cluster, Author is Bagley, Mark C.; Dale, James W.; Jenkins, Robert L.; Bower, Justin, which mentions a compound: 76632-23-0, SMILESS is OCC1=CSC(C)=N1, Molecular C5H7NOS, Recommanded Product: 76632-23-0.

The pyridine-containing central domain I (SEM = CH2OCH2CH2SiMe3) of amythiamicin A (thiopeptide antibiotic) is prepared in protected form in 9 steps with 93% enantiomeric excess and 18% overall yield from (S)-2-[1-(tert-butoxycarbonylamino)-2-methylpropyl]thiazole-4-carboxylic acid. Key reaction steps were Michael addition and cyclodehydration between enamine II and propynone III.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Peroxide-induced reduction of 9,10-anthraquinone by sodium borohydride in diglyme》. Authors are Panson, Gilbert S.; Weill, C. Edwin.The article about the compound:(2-Methylthiazol-4-yl)methanolcas:76632-23-0,SMILESS:OCC1=CSC(C)=N1).Related Products of 76632-23-0. Through the article, more information about this compound (cas:76632-23-0) is conveyed.

9,10-Anthraquinone (I) is not reduced at 20° by NaBH4 in pure diglyme [O(CH2CH2OMe)2] (II). In the presence of peroxides I is reduced to 9,10-anthradiol (III). When 0.25 g. NaBH4 is added to 1 g. I in 20 cc. II which has been exposed to air for several weeks a vigorous exothermic reaction sets in and the solution turns deep red. The mixture is stirred in an Ar atm. 45 min. and poured into 500 cc. cold N HCl, causing the precipitation of 0.9 g. III, m. 157-80°, which, on recrystallization from EtOH, yields I again. In a similar experiment, treating the reaction mixture with 5 cc. Ac2O and 3 g. fused NaOAc, heating it 0.5 hr. at 70° in an Ar atm., and pouring it into ice-H2O give 0.8 g. III diacetate, needles, m. 268-71° (decomposition). A possible mechanism for the peroxide-promoted reduction may be the cleavage of the solvent to aldehydes by a peroxide-induced action followed by conversion of the aldehydes so formed to alkoxyborohydrides which are the effective reducing agents.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

SDS of cas: 76632-23-0. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: (2-Methylthiazol-4-yl)methanol, is researched, Molecular C5H7NOS, CAS is 76632-23-0, about 4-Hydroxy-5,6-dihydropyrones as inhibitors of HIV protease: the effect of heterocyclic substituents at C-6 on antiviral potency and pharmacokinetic parameters. Author is Hagen, Susan E.; Domagala, John; Gajda, Christopher; Lovdahl, Michael; Tait, Bradley D.; Wise, Eric; Holler, Tod; Hupe, Donald; Nouhan, Carolyn; Urumov, Andrej; Zeikus, Greg; Zeikus, Eric; Lunney, Elizabeth A.; Pavlovsky, Alexander; Gracheck, Stephen J.; Saunders, James; VanderRoest, Steve; Brodfuehrer, Joanne.

Due largely to the emergence of multi-drug-resistant HIV strains, the development of new HIV protease inhibitors remains a high priority for the pharmaceutical industry. Toward this end, the authors previously identified a 4-hydroxy-5,6-dihydropyrone lead compound (CI-1029) which possesses excellent activity against the protease enzyme, good antiviral efficacy in cellular assays, and promising bioavailability in several animal species. The search for a suitable back-up candidate centered on the replacement of the aniline moiety at C-6 with an appropriately substituted heterocycle. In general, this series of heterocyclic inhibitors displayed good activity (in both enzymic and cellular tests) and low cellular toxicity; furthermore, several analogs exhibited improved pharmacokinetic parameters in animal models. The compound with the best combination of high potency, low toxicity, and favorable bioavailability was (S)-3-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one (I). This thiophene derivative also exhibited excellent antiviral efficacy against mutant HIV protease and resistant HIV strains. For these reasons, I was chosen for further preclin. evaluation.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem