Iodine-catalyzed stereoselective synthesis of allylglycosides, glycosyl cyanides and glycosyl azides

Iodine efficiently catalyzes the glycosidation of glycals with allyltrimethylsilane, trimethylsilyl cyanide and trimethylsilyl azide in dichloromethane at ambient temperature to afford the corresponding 2,3-unsaturated allyl glycosides, glycosyl cyanides and glycosyl azides in excellent yields with...

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Bibliographic Details
Published inSynlett no. 10; pp. 1638 - 1640
Main Authors Yadav, JS, Reddy, BVS, Rao, CV, Chand, PK, Prasad, AR
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MILD
ROUTE
F-RING
C-glycosides
iodine
Ferrier rearrangement
glycals
STEREOCONTROLLED SYNTHESIS
C-GLYCOSIDATION
SUBUNIT
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Summary:Iodine efficiently catalyzes the glycosidation of glycals with allyltrimethylsilane, trimethylsilyl cyanide and trimethylsilyl azide in dichloromethane at ambient temperature to afford the corresponding 2,3-unsaturated allyl glycosides, glycosyl cyanides and glycosyl azides in excellent yields with high alpha -selectivity.
ISSN:0936-5214
DOI:10.1055/s-2001-17438