Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 3, Pages 403-411Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200800991
Keywords
Carbohydrates; Glycosides; Regioselectivity; Glycosylation; myo-Inositol; n-Pentenyl orthoester; Thioglycoside; Donor-acceptor systems
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Funding
- Ministerio de Ciencia y Tecnologia (MCYT) [CTQ-2006-C03]
- US National Science Foundation [CHE-0243436]
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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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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