Wang, Lei Hashidoko, Yasuyuki Hashimoto, Makoto Cosolvent-Promoted O‑Benzylation with Silver(I) Oxide: Synthesis of 1′-Benzylated Sucrose Derivatives, Mechanistic Studies, and Scope Investigation A cosolvent-promoted O-benzylation strategy with Ag<sub>2</sub>O was developed. The cosolvent consisting of CH<sub>2</sub>Cl<sub>2</sub> and <i>n</i>-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. application scope;carbohydrate;benzyl bromides;Derivative;trifluoromethyl;ribose derivatives;Scope Investigation;reaction solubility;CH 2 Cl 2;mechanism;strategy;Synthesi;sucrose;benzylation efficiency;Oxide;Sucrose;Mechanistic Studies;method;hexane;Benzylated;Ag 2 O;photoreactive;formation;byproduct;cosolvent;glucose;benzylated 2016-05-05
    https://acs.figshare.com/articles/journal_contribution/Cosolvent-Promoted_O_Benzylation_with_Silver_I_Oxide_Synthesis_of_1_-Benzylated_Sucrose_Derivatives_Mechanistic_Studies_and_Scope_Investigation/3386170
10.1021/acs.joc.6b00144.s001