5987-55-3Relevant academic research and scientific papers
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.
Regioselective, Tin-Free Sulfation of Unprotected Hexopyranosides by Using Phenylboronic Acid
Fukuhara, Kenji,Shimada, Naoyuki,Nishino, Takashi,Kaji, Eisuke,Makino, Kazuishi
supporting information, p. 902 - 905 (2016/03/01)
Regioselective, tin-free sulfation of a number of unprotected glycopyranosides derived from L-fucose, L-rhamnose, D-arabinose, D-glucose, D-galactose, and D-trehalose was achieved by using phenylboronic acid for masking the hydroxy groups and a 2,2,2-trichloroethyl-protected sulfurylimidazolium salt as the sulfating reagent. The formation of phenylborate ester remarkably improved the solubility of the carbohydrates in organic solvents and indicated high reactivity and regioselectivity in the sulfation reactions. This methodology was successfully adapted to result in a one-pot procedure that did not require separation or purification of the reaction intermediates.
