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BiBr 3 ‐Promoted Activation of Peracetylated Glycosyl Iodides: Straightforward Access to Synthetically Useful 2‐ O ‐Deprotected Allyl Glycosides
Author(s) -
Pastore Antonello,
Adinolfi Matteo,
Iadonisi Alfonso
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.200800914
Subject(s) - chemistry , glycosyl , anomer , glycoside , glycosyl donor , reactivity (psychology) , combinatorial chemistry , organic chemistry , stereochemistry , medicine , alternative medicine , pathology
Substoichiometric amounts of BiBr 3 are able to promote anomeric activation of acetylated glycosyl iodides. This reactivity can be exploited for straightforward access to allyl glycosides unprotected at the O‐2 position. The reported protocol appears to be convenient in comparison with the pre‐existing ones in that shorter experimental times are needed and the use of strong acids is avoided. Suitable structural features of substrates (6‐deoxy sugars or use of benzoyl or methoxycarbonyl 2‐ O ‐participating groups) switch the process to a preferential glycosidation without deprotection at the O‐2 position.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)