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On the Gluco/Manno Paradox: Practical α‐Glucosylations by NIS/TfOH Activation of 4,6‐ O ‐Tethered Thioglucoside Donors
Author(s) -
Heuckendorff Mads,
Jensen Henrik H.
Publication year - 2016
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.201600899
Subject(s) - chemistry , triflic acid , anomer , context (archaeology) , glycosylation , stereochemistry , mannose , carbohydrate chemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry , paleontology , biology
A practical protocol for obtaining α‐glucosides was established. It was found that 4,6‐ O ‐benzylidene or 4,6‐ O ‐(di‐ tert ‐butylsilylene) tethering of glucosyl donors of the thioglycoside type enables highly α‐selective glucosylation under conditions of N ‐iodosuccinimide (NIS)/triflic acid (TfOH) activation. The α‐glucosylations were further found to be largely independent of promoter system, temperature, leaving group and anomeric configuration. The results are discussed in the context of the Glucose/Mannose paradox in glycosylation chemistry.