81058-28-8Relevant articles and documents
Effective 1,2-trans-Glycosylation of Complex Alcohols and Phenols Using the Oximate Orthoester of O-Pivaloyl Glucopyranose
Kunz, Horst,Pfrengle, Waldemar
, p. 713 - 714 (1986)
The highly stereoselective β-glycosylation of the complex steroid alcohols (2b)-(2d), the steroid phenol (2e), and the serine derivative (2f) is achieved in high yields using the new glycosyl donor 1,2-O-(1-N-1-phenylethylideneamino-oxy)-2,2-dimethylpropy
Glycoside Synthesis Using 2,3,4,6-Tetra-O-pivaloyl-α-D-glucopyranosyl Bromide
Kunz, Horst,Harreus, Albrecht
, p. 41 - 48 (2007/10/02)
In the presence of silver salts the glycosylation of benzyl alcohol and of cholesterol is achieved in high yields by use of 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide (2).The formation of orthoesters, which often complicates the Koenigs-Knorr reaction using 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (5), is largely suppressed using 2.The preferential formation of the glycoside from the intermediate ion A is a result of the steric influence of the tert-butyl substituent which hinders nucleophilic attack at the acyloxonium carbon atom and steers the reaction in the desired direction.
