875668-29-4

Basic information

• Product Name: (S)-2-[(3-benzyloxycarbonylamino-3-methoxycarbonyl-propyl)-methoxy-phosphinoylmethyl]-pentanedioic acid
• Synonyms: (S)-2-[(3-benzyloxycarbonylamino-3-methoxycarbonyl-propyl)-methoxy-phosphinoylmethyl]-pentanedioic acid
• CAS NO: 875668-29-4
• Molecular Weight: 487.444
• Mol File: 875668-29-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (S)-2-[(3-benzyloxycarbonylamino-3-methoxycarbonyl-propyl)-methoxy-phosphinoylmethyl]-pentanedioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-[(3-benzyloxycarbonylamino-3-methoxycarbonyl-propyl)-methoxy-phosphinoylmethyl]-pentanedioic acid(875668-29-4)
• EPA Substance Registry System: (S)-2-[(3-benzyloxycarbonylamino-3-methoxycarbonyl-propyl)-methoxy-phosphinoylmethyl]-pentanedioic acid(875668-29-4)

Safety Data

• Hazardous Substances Data: 875668-29-4(Hazardous Substances Data)

Upstream product

• 104523-60-6 (2S)-2-benzyloxycarbonylamino-4-phenylselenyl-butyric acid methyl ester 
• 501-53-1 benzyl chloroformate 
• 75266-39-6 methyl (S)-2-<<(benzyloxy)carbonyl>amino>-4-(methylsulfinyl)butanoate 
• 15159-67-8 (2S)-2-benzyloxycarbonylamino-4-bromo-butyric acid methyl ester 
• 5621-44-3 dimethyl 2-methylenepentanedioate 
• 864682-69-9 (S)-2-benzyloxycarbonylamino-4-hydroxyphosphinoyl-butyric acid methyl ester 
• 75266-40-9 N-benzyloxycarbonyl-L-α-vinylglycine methyl ester 

Downstream Products

• 864683-01-2 (S)-2-[(3-benzyloxycarbonylamino-3-methoxycarbonyl-propyl)-methoxy-phosphinoylmethyl]-pentanedioic acid dimethyl ester 

Relevant articles and documents

Prodrug forms of N-[(4-deoxy-4-amino-10-methyl)pteroyl]glutamate-γ- [ψP(O)(OH)]-glutarate, a potent inhibitor of folylpoly-γ-glutamate synthetase: Synthesis and hydrolytic stability

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.