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Methyl 2,3,6-trideoxy-2,3-epimino-α-D-allopyranoside

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
8
Issue
4
Identifiers
DOI: 10.1016/s0008-6215(00)81524-4

Abstract

Abstract The reduction of methyl 2-benzamido-2-deoxy-3,4,6-tri- O-methanesulphonyl-α- D-glucopyranoside with lithium aluminium hydride gave methyl 2,3,6-trideoxy-2,3-epimino-α- D-allopyranoside. The structure of the epimine was proved by an unequivocal synthesis from methyl 2,3-acetylepimino-4,6- O-benzylidene-2,3-dideoxy-α- D-allopyranoside by removal of the benzylidene substituent with N-bromosuccinimide, followed by reductive dehalogenation of the resulting 6-bromo derivative and the removal of the 4- O-benzoyl and N-acetyl substituents.

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