142811-51-6

Basic information

• Product Name: L-Glutamic acid, N-[4-[[2-amino-3-[(2,5-diamino-1,6-dihydro-6-oxo-4-pyrimidinyl)amino] propyl]amino]benzoyl]-, (S)-
• CAS NO: 142811-51-6
• Molecular Formula: C19H26N8O6
• Molecular Weight: 462.465
• Mol File: 142811-51-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: L-Glutamic acid, N-[4-[[2-amino-3-[(2,5-diamino-1,6-dihydro-6-oxo-4-pyrimidinyl)amino] propyl]amino]benzoyl]-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Glutamic acid, N-[4-[[2-amino-3-[(2,5-diamino-1,6-dihydro-6-oxo-4-pyrimidinyl)amino] propyl]amino]benzoyl]-, (S)-(142811-51-6)
• EPA Substance Registry System: L-Glutamic acid, N-[4-[[2-amino-3-[(2,5-diamino-1,6-dihydro-6-oxo-4-pyrimidinyl)amino] propyl]amino]benzoyl]-, (S)-(142811-51-6)

Safety Data

• Hazardous Substances Data: 142811-51-6(Hazardous Substances Data)

Upstream product

• 142811-48-1 [(R)-2-(2-Amino-5-nitro-6-oxo-1,6-dihydro-pyrimidin-4-ylamino)-1-formyl-ethyl]-benzyl-carbamic acid tert-butyl ester 
• 142811-47-0 2-amino-6-<<2'(R)--3'-hydroxypropyl>amino>-5-nitro-4(3H)-pyrimidinone 
• 142811-46-9 2-amino-6<<2'(R)-(benzylamino)-3'-hydroxypropyl>amino>-5-nitro-4(3H)-pyrimidinone 
• 142811-49-2 N-<4-<<2(S)--3-<(2-amino-5-nitro-4(3H)-oxopyrimidin-6-yl)amino>propyl>amino>benzoyl>-L-glutamic acid 
• 142811-50-5 N-<4-<<2(S)-(benzylamino)-3-<(2-amino-5-nitro-4(3H)-oxopyrimidin-6-yl)amino>propyl>amino>benzoyl>-L-glutamic acid 
• 142811-48-1 [(S)-2-(2-Amino-5-nitro-6-oxo-1,6-dihydro-pyrimidin-4-ylamino)-1-formyl-ethyl]-benzyl-carbamic acid tert-butyl ester 
• 142811-49-2 N-<4-<<2(R)--3-<(2-amino-5-nitro-4(3H)-oxopyrimidin-6-yl)amino>propyl>amino>benzoyl>-L-glutamic acid 
• 4271-30-1 N-(4-aminobenzoyl)-L-glutamic acid 
• 142811-50-5 N-<4-<<2(R)-(benzylamino)-3-<(2-amino-5-nitro-4(3H)-oxopyrimidin-6-yl)amino>propyl>amino>benzoyl>-L-glutamic acid 

Downstream Products

• 58-05-9 <6S>-N⁵-formyltetrahydrofolic acid 
• 135-16-0 (6S,S)-5,6,7,8-tetrahydrofolic acid 
• 142811-42-5 (S)-2-{4-[(S)-2-Amino-3-(2-amino-5-hydroxy-6-oxo-1,6-dihydro-pyrimidin-4-ylamino)-propylamino]-benzoylamino}-pentanedioic acid 
• 31690-11-6 N⁵,N¹⁰-methylenetetrahydrofolate 
• 4033-27-6 (S)-2-{4-[(2-Amino-4-oxo-3,4,7,8-tetrahydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid 
• 74708-38-6 (6R,S)-5,6,7,8-tetrahydrofolic acid 

Relevant articles and documents

Synthesis of Tetrahydropteridine C6-Stereoisomers, Including N5-Formyl-(6S)-tetrahydrofolic Acid

Chiral N1-protected vicinal diamines derived from amino acids were condensed with 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone, the nitro group reduced, and the amine deprotected.Oxidative cyclization of the resulting triaminopyrimidinone via quinoid pyrimidine intermediates gave a quinoid dihydropteridine, which was then reduced to a tetrahydropteridine C6-stereoisomer.Thus, 6(R)- and 6(S)-propyltetrahydropterin were stereospecifically synthesized (99 percent enantiomeric purity) in good yield from D- and L-norvaline, respectively.Reductive alkylation of (p-aminobenzoyl)-L-glutamate with a niropyrimidine aldehyde derived from D- or L-serine similarly afforded, after cyclization and reduction, (6R)- or (6S)-tetrahydrofolic acid.The latter was then converted to the natural isomer of leucovorin by regioselective N5-formylation with carbonyl diimidazole / formic acid without loss of enantiomeric purity.