A. Arasappan et Pl. Fuchs, REGIOSPECIFIC 4,6-FUNCTIONALIZATION OF PYRANOSIDES VIA DIMETHYLBORON - BROMIDE-MEDIATED CLEAVAGE OF PHTHALIDE ORTHOESTERS, Journal of the American Chemical Society, 117(1), 1995, pp. 177-183
An efficient strategy for regiocontrolled differentiation of the 4,6-p
ositions of pyranosides has been developed using dimethylboron bromide
-mediated cleavage of phthalide orthoesters. The reaction proceeds und
er mild conditions, is tolerant of additional acetal functionality, an
d produces a benzoate bearing suitable functionality for intramolecula
r assisted cleavage in the presence of SAc, OAc, and NHAc groups.