136210-13-4

Basic information

• Product Name: Benzoic acid, 4-[2-[(6S)-2-amino-1,4,5,6,7,8-hexahydro-4-oxopyrido[2,3-d]pyrimidin- 6-yl]ethyl]-
• CAS NO: 136210-13-4
• Molecular Formula: C16H18N4O3
• Molecular Weight: 314.344
• Mol File: 136210-13-4.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-[2-[(6S)-2-amino-1,4,5,6,7,8-hexahydro-4-oxopyrido[2,3-d]pyrimidin- 6-yl]ethyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-[2-[(6S)-2-amino-1,4,5,6,7,8-hexahydro-4-oxopyrido[2,3-d]pyrimidin- 6-yl]ethyl]-(136210-13-4)
• EPA Substance Registry System: Benzoic acid, 4-[2-[(6S)-2-amino-1,4,5,6,7,8-hexahydro-4-oxopyrido[2,3-d]pyrimidin- 6-yl]ethyl]-(136210-13-4)

Safety Data

• Hazardous Substances Data: 136210-13-4(Hazardous Substances Data)

Upstream product

• 127633-59-4 (S)-4-<2-(2-Amino-1,4,5,6,7,8-hexahydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)ethyl>benzonitrile 
• 4654-39-1 4-bromophenethanol 
• 84913-19-9 4-methylbenzene sulfonic acid 2-(4-bromophenyl)ethyl ester 
• 127633-43-6 2-<2-(4-Bromophenyl)ethyl>-1,3-propanediol 
• 127633-42-5 2-<2-(4-Bromophenyl)ethyl>propanedioic acid diethyl ester 
• 132554-00-8 (S)-(+)-2-<2-(4-Bromophenyl)ethyl>-1,3-propanediol acetate methanesulfonate 
• 127633-44-7 (R)-(+)-2-<2-(4-Bromophenyl)ethyl>-1,3-propanediol monoacetate 
• 127633-47-0 (R)-(+)-β-(Azidomethyl)-4-bromobenzenebutanol 
• 127633-49-2 (3RS,5S)-5-<2-(4-Bromophenyl)ethyl>-2-oxo-3-piperidinecarboxylic acid ethyl ester 
• 127633-50-5 (S)-2-Amino-6-<2-(4-bromophenyl)ethyl>-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-4(3H)-one 
• 127633-57-2 (S)-<2-(Azidomethyl)-4-(4-bromophenyl)butyl>propanedioic acid diethyl ester 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 

Downstream Products

• 110672-49-6 (S)-2-{4-[2-((R)-2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-yl)-ethyl]-benzoylamino}-pentanedioic acid diethyl ester 
• 110672-50-9 (S)-2-{4-[2-((S)-2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-yl)-ethyl]-benzoylamino}-pentanedioic acid diethyl ester 
• 95693-76-8 lometrexol 
• 106400-18-4 (6S)-5,10-dideaza-5,6,7,8-tetrahydrofolic acid 
• 866557-09-7 (6S)-5,10-dideaza-5,6,7,8-tetrahydropteroyl-L-glutamate-γ-L-glutamate 

Relevant articles and documents

Synthesis of (6R)- And (6S)-5,10-dideazatetrahydrofolate oligo-γ-glutamates: Kinetics of multiple glutamate ligations catalyzed by folylpoly-γ-glutamate synthetase

Folylpoly-γ-glutamate synthetase (FPGS, EC 6.3.2.17) catalyzes the ATP-dependent ligation of glutamic acid to reduced folates including (6S)-5,6,7,8-tetrahydrofolate (H4PteGlu), as well as to anticancer drugs such as 5,10-dideaza-5,6,7,8-tetrahydrofolate ((6R)-DDAH 4PteGlu1, (6R)-DDATHF, Lometrexol(tm)). Synthesis of unlabeled mono- and polyglutamates, DDAH4PteGlu n (6R, n = 1-6; 6S, n = 1-2), as well as (6R)-DDAH 4Pte[14C]Glu1, was effected from (6R)- or (6S)-5,10-dideazatetrahydropteroyl azide and glutamic acid, H-Glu-γ- Glun-y-Glu-OH (n = 0-4), or [14C]glutamic acid, respectively. These compounds were evaluated as FPGS substrates to determine steady-state kinetic constants. Michaelis-Menten kinetics were observed for (6-R)-DDAH4PteGlu1, the isomer corresponding to H 4PteGlu, whereas marked substrate inhibition was observed for (6S)-DDAH4PteGlun (n = 1-2) and (6R)-DDAH 4PteGlun (n = 2-5), but not (6.R)-DDAH 4PteGlu6. Multiple ligation of glutamate renders a quantitative analysis of these data difficult. However, approximate values of KM = 0.65-1.6 μM and K1, = 144-417 μM for DDAH 4PteGln were obtained using a simple kinetic model. The Royal Society of Chemistry 2005.

Asymmetric synthesis of lometrexol ((6R)-5,10-dideaza-5,6,7,8-tetrahydrofolic acid)

An enantioselective synthesis of lometrexol (1) which utilizes (5R)-2-piperidone 18 as a key intermediate is described. Lipase-catalyzed enantioselective esterification of 1,3-propanediol derivative 5 provided (R)-(+)-6, the absolute configuration of whic

Asymmetric synthesis and absolute configuration of 5,10-dideaza-5,6,7,8-tetrahydropteroic acid and 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF)

Lipase-catalyzed enantioselective esterification of 2-substituted 1,3-diols has been utilized in the asymmetry synthesis and consequent configurational assignments of the title compounds.