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Synthesis of 1,6-Dideoxynojirimycin, 1,6-Dideoxy-D-allo-nojirimycin, and 1,6-Dideoxy-D-gulo-nojirimycin via Asymmetric Hetero-Diels-Alder Reactions

✍ Scribed by Albert Defoin; Hervé Sarazin; Jacques Streith

Publisher: John Wiley and Sons
Year: 1996
Tongue: German
Weight: 503 KB
Volume: 79
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19960790223

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✦ Synopsis

Abstract

Asymmetric Diels‐Alder reaction of sorbaldehyde O‐methyloxime 1d with chiral chloronitroso derivative 2 of D‐mannose, followed by osmylation of the primary cycloadduct, led to diol 6a with excellent enantioselectivity (ee > 99%; Scheme 1). Catalytic hydrogenolysis of 6a gave 1,6‐dideoxy‐D‐allo‐nojirimycin (7a). Nucleophilic ring opening of cyclic sulfate 8 allowed a straightforward synthesis of 1,6‐dideoxynojirimycin (11) and of 1,6‐dideoxy‐D‐gulo‐nojirimycin (12; Scheme 2).

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## Abstract For Abstract see ChemInform Abstract in Full Text.