Beta-glycosidation of sterically hindered alcohols.
The 2-chloro-2-methylpropanoic ester serves as a steering group in the Schmidt glycosidation reaction. Rapid and efficient glycosidation of a range of sterically hindered alcohols takes place under mild, acidic conditions to afford the glycoside products in high yield and beta-selectivity and without formation of orthoester side products. The 2-chloro-2-methylpropanoic ester is readily cleaved under mild, basic conditions.
Szpilman
Alex M
AM
Laboratorium für Organische Chemie der ETH-Zürich, HCI H 335, Wolfgang Pauli Strasse 10, CH-8093 Zurich, Switzerland.
Carreira
Erick M
EM
D000438:Alcohols / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D006031:Glycosylation; D015394:Molecular Structure; D011422:Propionates / Q000737:chemistry*; D013237:Stereoisomerism
C539662:2-chloro-2-methylpropanoic acid; D000438:Alcohols; D011422:Propionates