Tetrahedron Letters p. 5001 - 5004 (1997)
Update date:2022-08-05
Topics:
Oshima, Kenji
Kitazono, Ei-Ichi
Aoyama, Yasuhiro
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.
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