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

Base Information

• Chemical Name: 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
• CAS No.: 155530-54-4
• Molecular Formula: C₄₂H₅₂N₂O₆Si
• Molecular Weight: 708.97
• Mol file: 155530-54-4.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 14 articles about 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 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: 90.0%

5-(N-benzylamino)-2-vinylpent-2(E)-enoic acid methyl ester (155530-53-3) + (R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-chlorocarbonyl-2,3-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (155530-51-1) → 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 (155530-54-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(00)75792-3

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 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 (155530-54-4)

Guidance literature:

Multi-step reaction with 6 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

3.1: 90 percent / H₂ / Pd/C / ethyl acetate / 22 h

4.1: 84 percent / NaBH₄ / HCl / ethanol / 1.47 h / -10 °C

5.1: oxalyl chloride / CH₂Cl₂ / 20 °C

6.1: 81 percent / Et₃N / benzene / 20 °C

With dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; hydrogen; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; hydrogenchloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; ethyl acetate; benzene;

DOI:10.1021/ja0202964

Reference yield:

(R)-5-hydroxymethylpyrrolidin-2-one (66673-40-3) → 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 (155530-54-4)

Guidance literature:

Multi-step reaction with 7 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

4.1: 90 percent / H₂ / Pd/C / ethyl acetate / 22 h

5.1: 84 percent / NaBH₄ / HCl / ethanol / 1.47 h / -10 °C

6.1: oxalyl chloride / CH₂Cl₂ / 20 °C

7.1: 81 percent / Et₃N / benzene / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; hydrogen; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; hydrogenchloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja0202964

upstream raw materials:

5-(N-benzylamino)-2-vinylpent-2(E)-enoic acid methyl ester

(R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-chlorocarbonyl-2,3-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

(R)-5-hydroxymethylpyrrolidin-2-one

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-1-(hex-5-enoyl)-4-oxo-2-vinyl-1,2,3,4,5,6,7,7a,10,10a-decahydropyrrolo[2.3-i]isoquinoline-8-carboxylate

methyl (2R,3aS,7aR,10aS)-5-benzyl-2-hydroxymethyl-1-(hex-5-enoyl)-4-oxo1,2,3,4,5,6,7,7a,10,10a-decahydropyrrolo[2.3-i]isoquinoline-8-carboxylate

(4aR,7aS,9R,10aS)-2-Benzyl-9-formyl-8-hex-5-enoyl-1-oxo-1,2,3,4,4a,7,7a,8,9,10-decahydro-pyrrolo[2,3-i]isoquinoline-5-carboxylic acid methyl ester