53638-83-8Relevant academic research and scientific papers
Polymer-bound carbonic anhydrides in N-acylation of 7-aminocephalosporanic acid.
Martin,Shambhu,Digenis
, p. 110 - 111 (1978)
Aminocephalosporanic acid tert-butyl ester was reacted with polystyrene-bound mixed carbonic-carboxylic anhydrides to give the corresponding N-acylated derivatives. Clevage of the tert-butyl protecting group with trifluoroacetic acid gave the corresponding cephalosporanic acid.
Enzymatic deprotection of the cephalosporin 3′-acetoxy group using Candida antarctica lipase B
Patterson, Leslie D.,Miller, Marvin J.
supporting information; experimental part, p. 1289 - 1292 (2010/04/29)
(Chemical Equation Presented) Cephalosporins remain one of themost 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 30-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.
