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ChemInform Abstract: 6-Deoxy-nojirimycin and 6-Deoxy-gulo-nojirimycin in the Racemic and D-Series, D-fuco-Nojirimycin and Their 1-Deoxyderivatives via Hetero-Diels—Alder Cycloadditions

✍ Scribed by A. DEFOIN; H. SARAZIN; J. STREITH

Publisher: John Wiley and Sons
Year: 2010
Weight: 36 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199805199

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ChemInform Abstract: 6-Deoxy-allo-nojiri

ChemInform Abstract: 6-Deoxy-allo-nojirimycin in the Racemic and D-Series, 6-Deoxy-D,L-talo-Nojirimycin, Their 1-Deoxyderivatives and 6-Deoxy-2-D,L-allosamine via Hetero-Diels—Alder Cycloadditions.

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Synthesis of 1,6-Dideoxynojirimycin, 1,6

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

✍ Albert Defoin; Hervé Sarazin; Jacques Streith 📂 Article 📅 1996 🏛 John Wiley and Sons 🌐 German ⚖ 503 KB

## 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