871733-36-7Relevant 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.
Visible-light-promoted conversion of alkyl benzyl ether to alkyl ester or alcohol via O-α-sp3 C-H cleavage
Lu, Ping,Hou, Tianyuan,Gu, Xiangyong,Li, Pixu
, p. 1954 - 1957 (2015/04/27)
A mild and high-yielding visible-light-promoted conversion of alkyl benzyl ethers to the alkyl esters or alkyl alcohols was developed. Mechanistic studies provided evidence for a radical chain reaction involving the homolytic cleavage of O-α-sp3 C-H bonds in the substrate as one of the propagation steps. We propose that α-bromoethers are key intermediates in the transformation.
New strategies for protecting group chemistry: Synthesis, reactivity, and indirect oxidative cleavage of para-siletanylbenzyl ethers
Tlais, Sami F.,Lain, Hubert,House, Sarah E.,Dudley, Gregory B.
scheme or table, p. 1876 - 1885 (2009/07/01)
Reported herein is a new entry in the growing arsenal of arylmethyl ether protecting groups. The parasiletanylbenzyl (PSB) ether is electronically similar to the benzyl ether. Cleavage of the PSB ether is accomplished under mild conditions-involving alkaline hydrogen peroxide - that are unique among cleavage protocols for arylmethyl ethers. Furthermore, the PSB group affords the user new flexibility in the implementation of protecting group strategies that revolve around multiple arylmethyl ether protecting groups. In addition to hydrogen peroxide-based cleavage protocols, conversion of a PSB ether into a para-methoxybenzyl (PMB) ether and assembly of a PSB ether from a pre-existing para-bromobenzyl (PBB) ether are described. Finally, a new reagent for installing PSB ethers under neutral "mix and heat" conditions is reported.
Iron(III) chloride-catalyzed reductive etherification of carbonyl compounds with alcohols
Iwanami, Katsuyuki,Yano, Kentaro,Oriyama, Takeshi
, p. 38 - 39 (2007/10/03)
A facile reductive etherification of carbonyl compounds can be performed by the reaction with alcohols and triethylsilane catalyzed by iron(III) chloride. The corresponding alkyl ethers are obtained in good to excellent yields under mild reaction conditions. Copyright
An efficient and convenient method for the direct conversion of alkyl silyl ethers into the corresponding alkyl ethers catalyzed by iron(III) chloride
Iwanami, Katsuyuki,Yano, Kentaro,Oriyama, Takeshi
, p. 2669 - 2672 (2007/10/03)
Various alcohol silyl ethers were readily and efficiently transformed into the corresponding alkyl ethers in high yields by the use of aldehydes combined with triethylsilane in the presence of a catalytic amount of iron(III) chloride. Georg Thieme Verlag Stuttgart.
