Complete regiospecificity in the benzylation of a cis-diol by the stannylidene procedure

1 January 1976

journal article
research article
Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications

No. 11,p. 375-376
https://doi.org/10.1039/c39760000375

Abstract

While conventional monobenzylation of benzyl 6-O-allyl-2-O-benzyl-α-D-galactopyranoside (1) gives a four component mixture, treatment of the OO′-dibutyl-stannylidene derivative of (1) with benzyl bromide provides only the 3-O-benzyl ether (2) in 66% isolated yield.

Keywords

TREATMENT
REGIOSPECIFICITY
CIS
GALACTOPYRANOSIDE
DIOL
MONOBENZYLATION
ETHER
PROCEDURE