Enzymatic deprotection of the cephalosporin 3'-acetoxy group using Candida antarctica lipase B.

The Journal of Organic Chemistry
Leslie D Patterson, Marvin J Miller

Abstract

Cephalosporins remain one of the most important classes of antibiotics. A useful site for derivatization involves generation of and chemistry at the 3'-hydroxymethyl position. While 3'-acetoxymethyl-substituted cephalosporins are readily available, deacetylation to access the free 3'-hydroxymethyl group is problematic when the carboxylic acid is protected as an ester. Herein we report that this important transformation has been efficiently accomplished using Candida antarctica lipase B. Although this transformation is difficult to carry out using chemical methods, the enzymatic deacetylation has been successful on gram scale, when the cephalosporin is protected as either the benzhydryl or tert-butyl esters and on the corresponding sulfoxide and sulfone of the tert-butyl ester.

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Citations

Nov 17, 2012·Chemical Reviews·Roman Bielski, Zbigniew Witczak
Aug 23, 2016·Organic Preparations and Procedures International·Kyle T Howard, John D Chisholm
Jan 11, 2013·Journal of the American Chemical Society·Qi WuManfred T Reetz
Oct 27, 2017·The Journal of Organic Chemistry·Aniket MishraIndubhusan Deb
Jul 7, 2020·Organic Letters·You-Ke ChenYi Lu

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