D. Kumagai et al., Cyclic di-t-butylsilylenediyl ether group as a convenient protective groupfor the glycoconjugate synthesis, TETRAHEDR L, 42(10), 2001, pp. 1953-1956
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.