title: Cosolvent-Promoted O-Benzylation with Silver(I) Oxide: Synthesis of 1'-Benzylated Sucrose Derivatives, Mechanistic Studies, and Scope Investigation.
abstract: A cosolvent-promoted O-benzylation strategy with Ag2O was developed. The cosolvent consisting of CH2Cl2 and n-hexane can not only improve the reaction solubility for carbohydrates but also increase the benzylation efficiency. The formation of byproducts is greatly inhibited in the developed method. This method is simple, mild, and highly effective, and numerous 1'-benzylated sucrose derivatives were prepared including a photoreactive (trifluoromethyl)phenyldiazirine-based sucrose. The mechanisms of benzylation with primary and secondary benzyl bromides were also elaborated. Furthermore, the application scope with alcohols, glucose, and ribose derivatives was investigated.
authors.affiliation: Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University , Kita 9, Nishi 9, Kita-ku, Sapporo 060-8589, Japan.
authors.forename: Lei
authors.initials: L
authors.lastname: Wang
authors.affiliation: Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University , Kita 9, Nishi 9, Kita-ku, Sapporo 060-8589, Japan.
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Hashidoko
authors.affiliation: Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University , Kita 9, Nishi 9, Kita-ku, Sapporo 060-8589, Japan.
authors.forename: Makoto
authors.initials: M
authors.lastname: Hashimoto