(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 3-benzyl ester 1 tert-butyl ester

Base Information

• Chemical Name: (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 3-benzyl ester 1 tert-butyl ester
• CAS No.: 449143-53-7
• Molecular Formula: C₃₄H₄₁NO₆Si
• Molecular Weight: 587.788
• Mol file: 449143-53-7.mol

Synonyms:(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 3-benzyl ester 1 tert-butyl ester

Chemical Property of (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 3-benzyl ester 1 tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 3-benzyl ester 1 tert-butyl ester

There total 8 articles about (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 3-benzyl ester 1 tert-butyl 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: 99.0%

(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester (138629-30-8) + benzyl chloroformate (501-53-1,94274-21-2) → (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 3-benzyl ester 1 tert-butyl ester (449143-53-7)

Guidance literature:

(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

benzyl chloroformate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.75h; Further stages.;

DOI:10.1021/ja0202964

Reference yield:

(R)-5-hydroxymethylpyrrolidin-2-one (66673-40-3) → (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 3-benzyl ester 1 tert-butyl ester (449143-53-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 95 percent / imidazole / dimethylformamide / 5 h / 20 °C

2.1: 93 percent / DMAP; triethylamine / CH₂Cl₂ / 0 - 20 °C

3.1: HMDS; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 99 percent / tetrahydrofuran; hexane / 0.75 h / -78 - 20 °C

With 1H-imidazole; dmap; n-butyllithium; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0202964

Reference yield:

(R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-2-one (138629-44-4) → (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 3-benzyl ester 1 tert-butyl ester (449143-53-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 93 percent / DMAP; triethylamine / CH₂Cl₂ / 0 - 20 °C

2.1: HMDS; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 99 percent / tetrahydrofuran; hexane / 0.75 h / -78 - 20 °C

With dmap; n-butyllithium; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/ja0202964

upstream raw materials:

2-oxo-3-phenylpropanenitrile

(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester

benzyl chloroformate

di-tert-butyl dicarbonate

Downstream raw materials:

1-tert-butyl 8-methyl (2R,3aS,7aR,10aS)-5-benzyl-2-[(tert-butyldiphenylsilanyloxy)methyl]-4-oxo-2,3,5,6,7,7a,10,10a-octahydropyrrolo[2.3-i]isoquinoline-1,8(4H)-dicarboxylate

methyl (2R,3aS,7aR,10aS)-5-benzyl-2-[(tert-butyldiphenylsilanyloxy)methyl]-1-(hex-5-enoyl)-4-oxo-1,2,3,4,5,6,7,7a,10,10a-decahydropyrrolo[2.3-i]isoquinoline-8-carboxylate

2(R)-4-{N-benzyl-N-[4'-methoxycarbonylhexa-3'(E),5'-dien-1'-yl]carbamoyl}-2-(tert-butyldiphenylsilanyloxymethyl)-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester

methyl (2R,3aS,7aR,10aS)-5-benzyl-2-[(tert-butyl-diphenylsilanyloxy)methyl]-4-oxo-1,2,3,4,5,6,7,7a,10,10a-decahydropyrrolo[2.3-i]isoquinoline-8-carboxylate