Forsman, Jonas J.;Waerna, Johan;Murzin, Dmitry Yu.;Leino, Reko published 《Reaction Kinetics and Mechanism of Sulfuric Acid-Catalyzed Acetolysis of Acylated Methyl L-Ribofuranosides》. The research results were published in《European Journal of Organic Chemistry》 in 2009.Application of 144490-03-9 The article conveys some information:
The mechanism of the sulfuric acid-catalyzed acetolysis of Me 2,3,5-tri-O-acetyl- and Me 2,3,5-tri-O-benzoyl-L-ribofuranosides and the accompanying anomerization of both the starting material and the 1,2,3,5-tetra-O-acetyl- and 1-O-acetyl-2,3,5-tri-O-benzoyl-L-ribofuranoses formed was investigated. The progress of the reactions was followed by 1H NMR spectroscopy and the rate constants for the reactions were determined for a proposed kinetic model. The role of H+ and Ac+ as the catalytically active species was clarified, proving that the anomerization of the acylated Me furanosides is activated by protonation, while, on the contrary, the anomerization of the 1-O-acetyl ribofuranoses is activated by the acetyl cation. The anomerization of the acylated Me furanosides was verified to be activated on the ring oxygen leading to endocyclic CO-bond rupture while the 1-O-acetyl ribofuranoses are activated on the acetyloxy group on C(1) leading to exocyclic cleavage. (© Wiley-VCH Verlag GmbH and Co. KGaA, 69451 Weinheim, Germany, 2009). And (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate (cas: 144490-03-9) was used in the research process.
(2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate(cas:144490-03-9 Application of 144490-03-9) is an isomer of 1,2,3,5-Tetra-O-acetyl β-D-Ribofuranose (T283100) which is used in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine.
Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem