87638-77-5Relevant articles and documents
Acyloxonium ions in the high-yielding synthesis of oxolanes from alditols, hexoses, and hexonolactones catalysed by carboxylic acids in anhydrous hydrogen fluoride
Defaye, Jacques,Gadelle, Andree,Pedersen, Christian
, p. 191 - 202 (2007/10/02)
Treatment of D-glucono-1,5- or D-mannono-1,4-lactone with anhydrous hydrogen fluoride catalysed by formic or acetic acid yields 3,6-anhydro-D-glucono- and -D-mannono-1,4-lactone, respectively.Similarly, D-mannitol is converted into 1,4-anhydro-D-mannitol and subsequently into the 1,4:3,6-dianhydride, whereas D-glucitol forms exclusively the 3,6-anhydride and, on further reaction, 1,4:3,6-dianhydro-D-glucitol.D-Glucose and 2-acetamido-2-deoxy-D-glucose are also converted into the corresponding 3,6-anhydrides by reaction with hydrogen fluoride and formic acid.13C-N.m.r. spectroscopy indicates that the reactions involve intermediate dioxolanyium ions.
Carbohydrates Containing the 2,6-Dioxabicyclooctane Skeleton: 3,6-Anhydrohexofuranose Derivatives with D-gluco, D-manno, L-ido, and L-gulo Configuration
Koell, Peter,Komander, Herbert,Meyer, Bernd
, p. 1310 - 1331 (2007/10/02)
All possible 3,6-anhydrofuranoses as well as their triacetates, methyl glycosides, and methyl diacetylglycosides have been prepared, some of them for the first time.This allowed an analysis of the equilibria of the anomers of the free sugars in water and