A Generalized Procedure for the One-Pot Preparation of Glycosyl Azides and Thioglycosides Directly from Unprotected Reducing Sugars under Phase-Transfer Reaction Conditions

Per‐O‐acetylated glycosyl azides and thioglycosides were prepared in excellent yield directly from unprotected reducing sugars through in situ generation of per‐O‐acetylated glycosyl bromides by a generalized one‐pot procedure under phase‐transfer conditions. Stereoselective products were formed wit...

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Bibliographic Details
Published inEuropean Journal of Organic Chemistry Vol. 2006; no. 1; pp. 74 - 79
Main Authors Kumar, Rishi, Tiwari, Pallavi, Maulik, Prakas R., Misra, Anup K.
Format Book Review Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.01.2006
WILEY‐VCH Verlag
Wiley
Subjects
Acylation
Carbohydrates
Chemistry
Chemistry, Organic
Glycoconjugate
Phase-transfer catalysis
Physical Sciences
Science & Technology
Synthetic methods
carbohydrates
ACTIVATION
ANALOGS
phase-transfer catalysis
CHIRAL TEMPLATES
acylation
FLUORIDES
STRECKER SYNTHESIS
glycoconjugate
CHEMOENZYMATIC SYNTHESIS
STEREOSELECTIVE-SYNTHESIS
GLYCOPROTEIN
GLYCOPEPTIDES
synthetic methods
ETHYL
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Summary:Per‐O‐acetylated glycosyl azides and thioglycosides were prepared in excellent yield directly from unprotected reducing sugars through in situ generation of per‐O‐acetylated glycosyl bromides by a generalized one‐pot procedure under phase‐transfer conditions. Stereoselective products were formed with complete inversion at the anomeric centers of the glycosyl bromides to provide a general high‐yielding procedure for the preparation of 1,2‐trans‐glycosyl azides and thioglycosides.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
Bibliography:CDRI communication no. 6854.
ark:/67375/WNG-V4F74ZMG-G
istex:CB5A42513B367240282A975BD070F92784B6626A
ArticleID:EJOC200500646
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200500646