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Catalytic Glycosylation with Glycosyl Thioimidate Donors
Author(s) -
LucasLopez Cristina,
Murphy Niamh,
Zhu Xiangming
Publication year - 2008
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.200800503
Subject(s) - glycosyl , chemistry , glycosylation , catalysis , glycosyl donor , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry
A new class of glycosyl thioimidates, glycosyl N ‐phenyl‐trifluorothioacetimidates, were prepared from the readily available glycosyl thiols in excellent yields. These imidates exhibited very good donor properties under the action of catalytic amounts of BF 3 · Et 2 O, and the corresponding glycosidation products were formed in very good to excellent yields. Thus, the first catalytic glycosylations with glycosyl thioimidate donors were achieved. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)