REGIOSPECIFIC 4,6-FUNCTIONALIZATION OF PYRANOSIDES VIA DIMETHYLBORON - BROMIDE-MEDIATED CLEAVAGE OF PHTHALIDE ORTHOESTERS

摘要

An efficient strategy for regiocontrolled differentiation of the 4,6-positions of pyranosides has been developed using dimethylboron bromide-mediated cleavage of phthalide orthoesters. The reaction proceeds under mild conditions, is tolerant of additional acetal functionality, and produces a benzoate bearing suitable functionality for intramolecular assisted cleavage in the presence of SAc, OAc, and NHAc groups. [References: 56]