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Reciprocal Donor–Acceptor Selectivity: the Influence of the Donor O‐2 Substituent in the Regioselective Mannosylation of myo ‐Inositol Orthopentanoate
Author(s) -
Uriel Clara,
Gómez Ana M.,
López J. Cristóbal,
FraserReid Bert
Publication year - 2009
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.200800991
Subject(s) - regioselectivity , chemistry , substituent , stereochemistry , glycosylation , pyridine , inositol , orthoester , acylation , glycosyl , selectivity , medicinal chemistry , organic chemistry , catalysis , biochemistry , receptor
The regioselectivity in the glycosylation of myo ‐inositol orthopentanoate with an n ‐pentenyl orthoester (NPOE) and an armed thioglycoside as glycosyl donors has been examined. The NPOE displayed higher regioselectivity and its preferred site for glycosidation coincided with that for selective acylation with RCOCl/pyridine. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)