56877-41-9Relevant articles and documents
Unusual orthogonality in the cleavage process of closely related chelating protecting groups for carboxylic acids by using different metal ions
Mundinger, Stephan,Jakob, Uwe,Bannwarth, Willi
supporting information, p. 1258 - 1262 (2014/04/03)
Three structurally related relay protecting groups for carboxylic acids that are based on chelating amines have been developed. These protecting groups can easily be introduced by coupling the carboxylic acid and the corresponding amine in the presence of 2-(1Hbenzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU). In addition to being stable to a whole array of reaction conditions, these protecting groups are also stable under acidic and basic conditions, allowing them to be used in combination with the ester protection of carboxylic acids. The cleavage of these protecting groups is activated by the chelation of metal ions, involving an unusual coordination of the amide nitrogen. Despite their similarity, cleavage of these protecting groups is possible in both a stepwise and an orthogonal fashion by applying different metal salts.
Cleavage of benzyloxycarbonyl-5-oxazolidinones to α-benzyloxycarbonylamino-α-alkyl esters by alcohols and sodium hydrogen carbonate
Allevi, Pietro,Cighetti, Giuliana,Anastasia, Mario
, p. 5319 - 5321 (2007/10/03)
The reaction of benzyloxycarbonyl-5-oxazolidinones with alcohols and sodium hydrogen carbonate to afford the corresponding benzyloxycarbonyl esters is described.
Methotrexate Analogues. 14. Synthesis of New γ-Substituted Derivatives as Dihydrofolate Reductase Inhibitors and Potential Anticancer Agents
Rosowsky, Andre,Forsch, Ronald,Uren, Jack,Wick, Michael
, p. 1450 - 1455 (2007/10/02)
The γ-tert-butyl ester (1), γ-hydrazide (2), γ-n-butylamide (3), and γ-benzylamide (4) derivatives of methotrexate (MTX) were synthesized from 4-amino-4-deoxy-N10-methylpteroic acid (APA) and the appropriate blocked L-glutamic acid precursors with the aid of the peptide bond forming reagent diethyl phosphorocyanidate.The affinity of these side chain modified products for dihydrofolate reductase (DHFR) from Lactobacillus casei and L1210 mouse leukemic cells was determined spectrophotometrically or by competitive radioligand binding assay, and their cytotoxicity was evaluated against L1210 leukemic cells in culture.The results provide continuing support for the view that the "γ-terminal region" of the MTX side chain is an attractive site for molecular modification of this anticancer agent.