Catalytic and stereoselective glycosylation with a novel and efficient disarmed glycosyl donor: Glycosyl p-trifluoromethylbenzylthio-p-trifluoromethylphenyl formimidate

A novel and efficient glycosyl donor having a p-trifluoromethylbenzylthio-p-trifluoroniethylphenyl formimidate function as a leaving group is easily prepared by the addition of anomeric hydroxyl group of 2,3,4,6-tetra-O-benzoyl-alpha,beta-D-glucopyranose to p-trifluoromethylphenyl isothiocyanate, fo...

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Bibliographic Details
Published inChemistry letters no. 3; pp. 392 - 393
Main Authors Mukaiyama, T, Chiba, H, Funasaka, S
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 05.03.2002
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
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Summary:A novel and efficient glycosyl donor having a p-trifluoromethylbenzylthio-p-trifluoroniethylphenyl formimidate function as a leaving group is easily prepared by the addition of anomeric hydroxyl group of 2,3,4,6-tetra-O-benzoyl-alpha,beta-D-glucopyranose to p-trifluoromethylphenyl isothiocyanate, followed by treatment with p-trifiuoromethylbenzyl bromide. Catalytic and stereoselective glycosylation using this glycosyl donor effectively proceeds by activating its nitorogen atom with various protic and Lewis acids.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2002.392