Cyclic di-t-butylsilylenediyl ether group as a convenient protective groupfor the glycoconjugate synthesis

Treatment of methyl B-D-glucopyranoside, methyl alpha -D-glucopyranoside, 2 -azido-2-deoxy-beta -D-galactopyranosyl fluoride, and 1,6-anhydro-beta -lac tose with di-t-butyldichlorosilane gave the corresponding 4.6-cyclic di-t-b utylsilylenediyl ether (4,6-CDBS) derivatives in high yields. It was sugges ted that the 4,6-CDBS group is quite stable under general conditions for fu rther chemical manipulations such as the acetylation, benzylation and glyco sylation reactions employed widely in the carbohydrate chemistry. This prot ective group was readily removed by treatment with tetrabutylammonium fluor ide or triethylamine-3HF complex under mild conditions. (C) 2001 Elsevier S cience Ltd. All rights reserved.