Chemistry of imino glycals: Preparation and application to the synthesis of (+)-fagomine

The synthesis of imino glucal 2 from tri-O-benzyl-D-glucal in 8 steps is described. This novel imino sugar building block is further converted into (+)-fagomine by a two-step hydrogenation sequence.

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Bibliographic Details
Published inSynlett no. 8; pp. 1329 - 1331
Main Authors Desire, J, Dransfield, PJ, Gore, PM, Shipman, M
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
carbohydrates
(+)-fagomine
1-DEOXYNOJIRIMYCIN
stereoselective synthesis
piperidines
1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL
FAGOMINE
imino glycals
GLYCOSIDASE INHIBITORS
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Summary:The synthesis of imino glucal 2 from tri-O-benzyl-D-glucal in 8 steps is described. This novel imino sugar building block is further converted into (+)-fagomine by a two-step hydrogenation sequence.
ISSN:0936-5214
DOI:10.1055/s-2001-16039