(2R,5S)-2-(Dimethoxy-phosphorylmethyl)-5-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyloxymethyl]-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2R,5S)-2-(Dimethoxy-phosphorylmethyl)-5-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyloxymethyl]-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 172885-74-4
• Molecular Formula: C₂₅H₄₁N₂O₉PSi
• Molecular Weight: 572.668
• Mol file: 172885-74-4.mol

Synonyms:(2R,5S)-2-(Dimethoxy-phosphorylmethyl)-5-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyloxymethyl]-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property of (2R,5S)-2-(Dimethoxy-phosphorylmethyl)-5-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyloxymethyl]-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S)-2-(Dimethoxy-phosphorylmethyl)-5-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyloxymethyl]-pyrrolidine-1-carboxylic acid benzyl ester

There total 11 articles about (2R,5S)-2-(Dimethoxy-phosphorylmethyl)-5-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyloxymethyl]-pyrrolidine-1-carboxylic acid benzyl ester 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: 38.0%

4-oxo-4-(2-(trimethylsilyl)ethoxy)butanoic acid (93790-78-4) + (2R,5S)-2-(Dimethoxy-phosphorylmethyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester (172885-71-1) → (2R,5S)-2-(Dimethoxy-phosphorylmethyl)-5-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyloxymethyl]-pyrrolidine-1-carboxylic acid benzyl ester (172885-74-4)

Guidance literature:

With diphenyl-phosphinic acid; triethylamine; In toluene; at 80 ℃; for 24h;

DOI:10.1021/jo951469t

Reference yield:

(2S,5R)-N-benzyl-5-methoxycarbonylproline (102572-59-8) → (2R,5S)-2-(Dimethoxy-phosphorylmethyl)-5-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyloxymethyl]-pyrrolidine-1-carboxylic acid benzyl ester (172885-74-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) Et₃N, ClCO₂Et, 2.) NaBH₄ / 1.) THF, 0 deg C, 3 h, 2.) H₂O, 0 deg C, 1 h

2: 2.40 g / imidazole / dimethylformamide / 24 h / 25 °C

3: DIBALH / toluene; hexane / 0.83 h / 25 °C

4: 100 percent / H₂ / Pd(OH)2/C / ethanol / 18 h / 25 °C / 760 Torr

5: 93 percent / Et₃N / CH₂Cl₂ / 18 h / 0 °C

6: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 deg C, 5 min; -78 deg C -> room temperature

7: 1.) NaH / 1.) DMF, 1 h, 2.) 0 deg C, 48 h

8: 1.) NaH / 1.) DMF, room temperature, 30 min, 2.) 30 min

9: 94 percent / Bu₃SnH, AIBN / toluene / 3 h / 115 °C

10: 95 percent / AcOH / tetrahydrofuran; H₂O / 24 h / 60 °C

11: 38 percent / Et₃N, DPPA / toluene / 24 h / 80 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); diphenyl-phosphinic acid; hydrogen; tri-n-butyl-tin hydride; chloroformic acid ethyl ester; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo951469t

Reference yield:

(2R,5S)-1-Benzyl-5-hydroxymethyl-pyrrolidine-2-carboxylic acid methyl ester (113304-86-2) → (2R,5S)-2-(Dimethoxy-phosphorylmethyl)-5-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyloxymethyl]-pyrrolidine-1-carboxylic acid benzyl ester (172885-74-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 2.40 g / imidazole / dimethylformamide / 24 h / 25 °C

2: DIBALH / toluene; hexane / 0.83 h / 25 °C

3: 100 percent / H₂ / Pd(OH)2/C / ethanol / 18 h / 25 °C / 760 Torr

4: 93 percent / Et₃N / CH₂Cl₂ / 18 h / 0 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 deg C, 5 min; -78 deg C -> room temperature

6: 1.) NaH / 1.) DMF, 1 h, 2.) 0 deg C, 48 h

7: 1.) NaH / 1.) DMF, room temperature, 30 min, 2.) 30 min

8: 94 percent / Bu₃SnH, AIBN / toluene / 3 h / 115 °C

9: 95 percent / AcOH / tetrahydrofuran; H₂O / 24 h / 60 °C

10: 38 percent / Et₃N, DPPA / toluene / 24 h / 80 °C

With 1H-imidazole; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); diphenyl-phosphinic acid; hydrogen; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo951469t

upstream raw materials:

4-oxo-4-(2-(trimethylsilyl)ethoxy)butanoic acid

(2R,5S)-2-(Dimethoxy-phosphorylmethyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

(2S,5R)-N-benzyl-5-methoxycarbonylproline

[(2R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-pyrrolidin-2-yl]-methanol

Downstream raw materials:

(2R,5S)-2-(Hydroxy-methoxy-phosphorylmethyl)-5-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyloxymethyl]-pyrrolidine-1-carboxylic acid benzyl ester