Organosilicon-mediated regioselective acetylation of carbohydrates
2012 (Engelska)Ingår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 48, nr 43, s. 5370-5372Artikel i tidskrift (Refereegranskat) 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.
Ort, förlag, år, upplaga, sidor
2012. Vol. 48, nr 43, s. 5370-5372
Nyckelord [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
Nationell ämneskategori
Kemi
Identifikatorer
URN: urn:nbn:se:kth:diva-100119DOI: 10.1039/c2cc31556dISI: 000303442500043Scopus ID: 2-s2.0-84860816249OAI: oai:DiVA.org:kth-100119DiVA, id: diva2:542846
Anmärkning
QC 20120803
2012-08-032012-08-032017-12-07Bibliografiskt granskad