117751-86-7

Basic information

• Product Name: 3-Butenoic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (2S)-
• CAS NO: 117751-86-7
• Molecular Formula: C16H21NO4
• Molecular Weight: 291.347
• Mol File: 117751-86-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 3-Butenoic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Butenoic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (2S)-(117751-86-7)
• EPA Substance Registry System: 3-Butenoic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (2S)-(117751-86-7)

Safety Data

• Hazardous Substances Data: 117751-86-7(Hazardous Substances Data)

Upstream product

• 78266-81-6 tert-butyl N-[(benzyloxy)carbonyl]-L-homoserinate 
• 5891-45-2 (S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester 
• 117751-84-5 1,1-dimethylethyl 4-(methylsulfinyl)-2-[[(phenylmethoxy)carbonyl]amino]-(2S)-butanoate 
• 16874-01-4 benzyl (S)-1-(tert-butoxycarbonyl)-3-(methylthio)propylcarbamate 
• 1152-62-1 Cbz-Met-OH 
• 60079-12-1 β-Methyl α-tert-butyl (2S)-N-(benzyloxycarbonyl)aspartate 
• 47307-26-6 (S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester 
• 3160-47-2 N-(benzyloxycarbonyl)-L-aspartic acid 4-methyl ester 
• 72289-51-1 tert-butyl (2S,3R)-2-(benzyloxycarbonyl)amino-3-hydroxybutanoate 
• 19728-63-3 N-benzyloxycarbonyl-L-treonine 
• 601491-39-8 tert-butyl (2S)-4-bromo-2-(N-benzyloxycarbonyl)aminobutyrate 
• 501-53-1 benzyl chloroformate 
• 438542-12-2 2-amino-4-bromo-butyric acid tert-butyl ester 
• 521302-84-1 tert-butyl (2S,3R)-2-(benzyloxycarbonyl)amino-3-iodobutanoate 

Downstream Products

• 75266-42-1 (S)-2-<(benzyloxycarbonyl)amino>-3-butenoic acid 
• 117751-75-4 2'(R),3'(S)-N-(2-acetoxy-3-benzyloxycarbonylamino-3-tert-butoxycarbonylpropyl)N-tert-butoxycarbonylglycine tert-butyl ester 
• 117772-22-2 2'(R),3'(S)-N-(3-benzyloxycarbonylamino-3-tert-butoxycarbonyl-2-hydroxypropyl)N-tert-butoxycarbonylglycine tert-butyl ester 
• 117751-74-3 2'(R),3'(S)-N-(3-benzyloxycarbonylamino-3-tert-butoxycarbonyl-2-hydroxypropyl)glycine tert-butyl ester 
• 875668-30-7 2-[(3-benzyloxycarbonylamino-3-tert-butoxycarbonyl-propyl)-hydroxy-phosphinoylmethyl]-pentanedioic acid di-tert-butyl ester 
• 875668-09-0 2-benzyloxycarbonylamino-4-hydroxyphosphinoyl-butyric acid tert-butyl ester 
• 117751-80-1 2(S)-tert-butyl 2-N-benzyloxycarbonylamino-3,4-epoxybutanoate 

Relevant articles and documents

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Ester prodrugs of the phosphinate pseudopeptide N-[(4-deoxy-4-amino-10- methyl)pteroyl]glutamate-γ-[ψP-(O)(OH)]-glutarate (1a) were synthesized. H-phosphinic acids derived from N-Cbz vinyl glycine esters were converted to the desired pseudopeptides by Michael addition to α-methyleneglutarate esters. Pivaloyloxymethyl (POM) ester moieties were incorporated in both the N-terminal and C-terminal fragments prior to formation of either C-P bond, N-Alkylation of the corresponding amides derived from N-(N-methyl)aminobenzoic acid with 2,4-diamino-6-(bromomethyl)pteridine gave the target compounds. POM esters of methotrexate and the corresponding γ-glutamyl conjugate were also synthesized using the same strategy. All prodrugs were evaluated in Chinese hamster ovary cells. Although the pseudopeptide prodrugs were ineffective, prodrugs of methotrexate and the corresponding γ-glutamyl conjugate were equipotent with the parent compounds. Stability of the prodrugs was investigated in both phosphate buffer and cell line medium to provide a rationale for the observed biological data.

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