jo6b00144_si_001.pdf (4.49 MB)
Cosolvent-Promoted O‑Benzylation with Silver(I) Oxide: Synthesis of 1′-Benzylated Sucrose Derivatives, Mechanistic Studies, and Scope Investigation
journal contribution
posted on 2016-05-05, 00:00 authored by Lei Wang, Yasuyuki Hashidoko, Makoto HashimotoA 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.
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application scopecarbohydratebenzyl bromidesDerivativetrifluoromethylribose derivativesScope Investigationreaction solubilityCH 2 Cl 2mechanismstrategySynthesisucrosebenzylation efficiencyOxideSucroseMechanistic StudiesmethodhexaneBenzylatedAg 2 Ophotoreactiveformationbyproductcosolventglucosebenzylated
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