5987-55-3Relevant articles and documents
Complexation-induced activation of sugar OH groups. Regioselective alkylation of methyl fucopyranoside via cyclic phenylboronate in the presence of amine
Oshima, Kenji,Kitazono, Ei-Ichi,Aoyama, Yasuhiro
, p. 5001 - 5004 (1997)
Methyl fucopyranoside undergoes highly regioselective 3-O-alkylation via complexation with phenylboronic acid, followed by treatment of the resulting 3,4-boronate with iodobutane in the presence of a tertiary amine and Ag2O. The essential step is suggested to be regioselective activation of the 3-O nucleophilic center upon amine coordination with the O-bonded boron atom.