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From Chitin to α‐Glycosides of N ‐Acetylglucosamine Using Catalytic Copper Triflate in a Heated Sealed‐Vessel Reactor
Author(s) -
Frem Dany,
Urban Dominique,
Norsikian Stéphanie,
Beau JeanMarie
Publication year - 2017
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.201700933
Subject(s) - chemistry , glycosylation , trifluoromethanesulfonate , n acetylglucosamine , copper , chitin , glycoside , catalysis , selectivity , glucosamine , organic chemistry , alcohol , combinatorial chemistry , biochemistry , chitosan , enzyme
The selective preparation of α‐glycosides of GlcNAc has been accomplished using a direct copper(II) triflate catalyzed glycosylation between α‐ d ‐glucosamine pentaacetate, readily available from chitin, and a range of alcohol acceptors. The α‐selectivity results from a post‐glycosylation anomerization.