2-[4-[(2-amino-5-formyl-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methylamino]benzoyl]aminopentanedioic acid

Base Information

• Chemical Name: 2-[4-[(2-amino-5-formyl-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methylamino]benzoyl]aminopentanedioic acid
• CAS No.: 54353-24-1
• Molecular Formula: C₂₀H₂₃N₇O₇
• Molecular Weight: 473.445
• Mol file: 54353-24-1.mol

Synonyms:D-Glutamicacid, N-[4-[[(2-amino-5-formyl-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-(9CI); Pteroyl-D-glutamic acid

Chemical Property of 2-[4-[(2-amino-5-formyl-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methylamino]benzoyl]aminopentanedioic acid

Chemical Property:

• Density: 1.68g/cm³

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[4-[(2-amino-5-formyl-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methylamino]benzoyl]aminopentanedioic acid

There total 25 articles about 2-[4-[(2-amino-5-formyl-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methylamino]benzoyl]aminopentanedioic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N-<4-<<2(S)--3-<(2-amino-5-nitro-4(3H)-oxopyrimidin-6-yl)amino>propyl>amino>benzoyl>-L-glutamic acid (142811-49-2) → <6S>-N5-formyltetrahydrofolic acid (58-05-9,22350-60-3,54353-24-1,68538-85-2,73951-54-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / aq. 1 M HCl / tetrahydrofuran / 2.5 h / 58 °C

2: 91 percent / hydrogen / 10percent Pd-C / dimethylformamide; aq. HCl / 25 h / 2327.2 Torr

4: 1,1'-carbonyl diimidazole / dimethylformamide

With hydrogenchloride; hydrogen; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; hydrogenchloride; N,N-dimethyl-formamide;

DOI:10.1021/jo00042a030

Reference yield:

2-amino-6<<2'(R)-(benzylamino)-3'-hydroxypropyl>amino>-5-nitro-4(3H)-pyrimidinone (142811-46-9) → <6S>-N5-formyltetrahydrofolic acid (58-05-9,22350-60-3,54353-24-1,68538-85-2,73951-54-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / 1 M aq. NaOH -> pH 9.5 / dioxane / 46 h / Ambient temperature

2: 5.01 g / Dess-Martin periodinane, AcOH / CH₂Cl₂ / 1.17 h / Ambient temperature

3: 2) NaBH₃CN / 1) DMF, 0 deg C, 5 min, 2) DMF, 0 deg C, 1 h

4: 98 percent / aq. 1 M HCl / tetrahydrofuran / 2.5 h / 58 °C

5: 91 percent / hydrogen / 10percent Pd-C / dimethylformamide; aq. HCl / 25 h / 2327.2 Torr

7: 1,1'-carbonyl diimidazole / dimethylformamide

With hydrogenchloride; sodium hydroxide; hydrogen; sodium cyanoborohydride; Dess-Martin periodane; acetic acid; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; hydrogenchloride; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00042a030

Reference yield:

2-amino-6-<<2'(R)--3'-hydroxypropyl>amino>-5-nitro-4(3H)-pyrimidinone (142811-47-0) → <6S>-N5-formyltetrahydrofolic acid (58-05-9,22350-60-3,54353-24-1,68538-85-2,73951-54-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 5.01 g / Dess-Martin periodinane, AcOH / CH₂Cl₂ / 1.17 h / Ambient temperature

2: 2) NaBH₃CN / 1) DMF, 0 deg C, 5 min, 2) DMF, 0 deg C, 1 h

3: 98 percent / aq. 1 M HCl / tetrahydrofuran / 2.5 h / 58 °C

4: 91 percent / hydrogen / 10percent Pd-C / dimethylformamide; aq. HCl / 25 h / 2327.2 Torr

6: 1,1'-carbonyl diimidazole / dimethylformamide

With hydrogenchloride; hydrogen; sodium cyanoborohydride; Dess-Martin periodane; acetic acid; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; hydrogenchloride; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00042a030

upstream raw materials:

tetrahydrofolic acid

formic acid

chloral

N-methyl-N-phenylformamide

Downstream raw materials:

(6RS)-5,10-diformyl-5,6,7,8-tetrahydrofolic acid

Refernces

• 1、 Brunner, Henri,Rosenboem, Sabine. "Enantioselective catalyses CXXXV [1]. Stereoselective hydrogenation of folic acid and 2-methylquinoxaline with optically active rhodium(I)-phosphane complexes". . p. 1371 - 1382. Retrieved 2007/10/03.
• 2、 Rees,Suckling,Wood. "A simple and effective method for preparation of the 6(R)- and 6(S)-diastereoisomers of 5-formyltetrahydrofolate (leucovorin)". . p. 470 - 472. Retrieved 2007/10/02.