121351-12-0Relevant articles and documents
Enantiomerically Pure, Highly Functionalized Tetrahydrofurans from Simple Carbohydrate Precursors
Lundt, Inge,Frank, Holger
, p. 13285 - 13298 (1994)
6-Bromo-6-deoxy-1,4-aldonolactones and 6-bromo-6-deoxy-alditols with D-galacto, D-altro-, D-manno- and D-ido-configuration were selectively converted into hydroxylated tetrahydrofuran derivatives by simple heating in water.The 6-bromo-6-deoxy-altritol (10) and 6-bromo-6-deoxy-D-iditol (25) reacted even at room temperature.Likewise, 6-bromo-2,6-dideoxy-aldonolactones with D-arabino- (29) and D-lyxo-configuration (31) gave the corresponding 2-deoxy-3,6-anhydride, when heated in water.The rate of formation of the furan ring by intramolecular nucleophilic substitution was determined by the conformation of the bromopolyols in water.
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.
