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

Kumar Rishi | Zendy; Tiwari Pallavi | Zendy; Maulik Prakas R. | Zendy; Misra Anup K. | Zendy

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

Author(s) -

Kumar Rishi,

Tiwari Pallavi,

Maulik Prakas R.,

Misra Anup K.

Publication year - 2006

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200500646

Subject(s) - chemistry , glycosyl , anomer , stereoselectivity , yield (engineering) , organic chemistry , azide , combinatorial chemistry , catalysis , materials science , metallurgy

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)

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