760987-62-0Relevant academic research and scientific papers
Cosolvent-Promoted O-Benzylation with Silver(I) Oxide: Synthesis of 1′-Benzylated Sucrose Derivatives, Mechanistic Studies, and Scope Investigation
Wang, Lei,Hashidoko, Yasuyuki,Hashimoto, Makoto
, p. 4464 - 4474 (2016/07/06)
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.
Chlorotrimethylsilane as a mild and effective source of acid catalyst in reductive benzylation
Izumi, Minoru,Fukase, Koichi
, p. 594 - 595 (2007/10/03)
New reductive benzylation of hydroxy functions was effected by using the combination of benzaldehyde, TMSCl, and Et3SiH. TMSCl first reacts with alcohols to form HCl, which is probably the ultimate catalyst for this reaction system. TMSCl can also trap water and thus effectively promote dehydration reactions when more than stoichiometric amount of TMSCl is used. Although excess TMSCl was required for the foregoing reactions, TMSCl could be readily removed by simple evaporation. Copyright
A Suzuki-Miyaura coupling mediated deprotection as key to the synthesis of a fully lipidated malarial GPI disaccharide
Liu, Xinyu,Seeberger, Peter H.
, p. 1708 - 1709 (2007/10/03)
Ligandless palladium-catalyzed Suzuki-Miyaura coupling converted an inert p-bromobenzyl ether to a DDQ-labile p-(3,4-dimethoxyphenyl) benzyl ether in the presence of azide functionality and this strategy serves as a key step for the convergent synthesis of a fully lipidated malaria GPI disaccharide.
