Application of Appel reaction to the primary alcohol groups of fructooligosaccharides: synthesis of 6,6â?6â²â?trihalogenated 1-kestose derivatives was written by Tachrim, Zetryana Puteri;Nakamura, Tadashi;Sakihama, Yasuko;Hashidoko, Yasuyuki;Hashimoto, Makoto. And the article was included in ARKIVOC (Gainesville, FL, United States) in 2018.Electric Literature of C18H32O16 This article mentions the following:
1-kestose (O-β-D-fructofuranosyl-(2â?)-β-D-fructofuranosyl-(2â?)-α-D-glucopyranoside) is a potential short chain fructooligosaccharide with an inulin-type skeleton. Halogenation of 1-kestose was conducted via the Appel reaction with the use of carbon tetrahalide (CBr4 or CCl4) and triphenylphosphine, which was then followed by conventional acetylation. The per-O-acetylated form of 6,6â?6â²â?trihalogenated derivatives of 1-kestose were conveniently isolated. Further deprotection of the per-O-acetylated form resulted in 6-, 6â?, and 6â²â?trihalogenated derivatives The structure elucidation by one- and two-dimensional NMR established that halogenation are specific at the 6-, 6â?, and 6â²â?position of 1-kestose primary alcs. In the experiment, the researchers used many compounds, for example, (2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 470-69-9Electric Literature of C18H32O16).
(2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-2-((((2R,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)methyl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 470-69-9) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. THF can also be synthesized by catalytic hydrogenation of furan. This allows certain sugars to be converted to THF via acid-catalyzed digestion to furfural and decarbonylation to furan, although this method is not widely practiced. THF is thus derivable from renewable resources.Electric Literature of C18H32O16
Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem