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Organosilicon-mediated regioselective acetylation of carbohydrates
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2012 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 48, no 43, 5370-5372 p.Article in journal (Refereed) Published
Abstract [en]

Organosilicon-mediated, regioselective acetylation of vicinal- and 1,3-diols is presented. Methyl trimethoxysilane or dimethyl dimethoxysilane was first used to form cyclic 1,3,2-dioxasilolane or 1,3,2-dioxasilinane intermediates, and subsequent acetate-catalyzed monoacylation was efficiently performed by addition of acetic anhydride or acetyl chloride under mild conditions. The reaction exhibited high regioselectivity, resulting in the same protection pattern as in organotin-mediated schemes.

Place, publisher, year, edition, pages
2012. Vol. 48, no 43, 5370-5372 p.
Keyword [en]
1, 3, 2 dioxasilinane, 1, 3, 2 dioxasilolane, acetic acid, acetic anhydride, carbohydrate, dimethyl dimethoxysilane, methyl trimethoxysilane, organosilicon derivative, unclassified drug, acetylation, acylation, article, catalysis, chemical bond, chemical modification, chemical structure, proton nuclear magnetic resonance, stereochemistry, substitution reaction
National Category
Chemical Sciences
URN: urn:nbn:se:kth:diva-100119DOI: 10.1039/c2cc31556dISI: 000303442500043ScopusID: 2-s2.0-84860816249OAI: diva2:542846
QC 20120803Available from: 2012-08-03 Created: 2012-08-03 Last updated: 2012-08-03Bibliographically approved

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