(R)-3-Benzylsulfanyl-2-{tert-butoxycarbonyl-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-cyano-butyryl]-amino}-propionic acid benzyl ester

Base Information

• Chemical Name: (R)-3-Benzylsulfanyl-2-{tert-butoxycarbonyl-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-cyano-butyryl]-amino}-propionic acid benzyl ester
• CAS No.: 158008-80-1
• Molecular Formula: C₃₃H₄₆N₂O₆SSi
• Molecular Weight: 626.89
• Mol file: 158008-80-1.mol

Synonyms:(R)-3-Benzylsulfanyl-2-{tert-butoxycarbonyl-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-cyano-butyryl]-amino}-propionic acid benzyl ester

Chemical Property of (R)-3-Benzylsulfanyl-2-{tert-butoxycarbonyl-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-cyano-butyryl]-amino}-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-Benzylsulfanyl-2-{tert-butoxycarbonyl-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-cyano-butyryl]-amino}-propionic acid benzyl ester

There total 11 articles about (R)-3-Benzylsulfanyl-2-{tert-butoxycarbonyl-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-cyano-butyryl]-amino}-propionic 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: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-3-Benzylsulfanyl-2-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-cyano-butyrylamino]-propionic acid benzyl ester (158008-79-8) → (R)-3-Benzylsulfanyl-2-{tert-butoxycarbonyl-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-cyano-butyryl]-amino}-propionic acid benzyl ester (158008-80-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 0.666667h; Ambient temperature;

DOI:10.1016/S0040-4039(00)73032-2

Reference yield:

3-hydroxyglutaronitrile (13880-89-2) → (R)-3-Benzylsulfanyl-2-{tert-butoxycarbonyl-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-cyano-butyryl]-amino}-propionic acid benzyl ester (158008-80-1)

Guidance literature:

Multi-step reaction with 7 steps

1: K₂CO₃ / H₂O / 120 h / Ambient temperature

2: 53 percent / dimethylformamide / 16 h / Ambient temperature

3: imidazole / dimethylformamide / 48 h / Ambient temperature

4: 1 N aq. HCl / methanol / 2 h / Ambient temperature

5: imidazole / dimethylformamide / 48 h / Ambient temperature

6: n-BuLi / tetrahydrofuran / -78 deg C; room temp., overnight

7: 98 percent / NEt₃, 4-DMAP / CH₂Cl₂ / 0.67 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; dmap; n-butyllithium; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)73032-2

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (R)-3-Benzylsulfanyl-2-{tert-butoxycarbonyl-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-cyano-butyryl]-amino}-propionic acid benzyl ester (158008-80-1)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / dimethylformamide / 48 h / Ambient temperature

2: n-BuLi / tetrahydrofuran / -78 deg C; room temp., overnight

3: 98 percent / NEt₃, 4-DMAP / CH₂Cl₂ / 0.67 h / Ambient temperature

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

DOI:10.1016/S0040-4039(00)73032-2

upstream raw materials:

di-tert-butyl dicarbonate

(R)-3-Benzylsulfanyl-2-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-cyano-butyrylamino]-propionic acid benzyl ester

3-hydroxyglutaronitrile

tert-butyldimethylsilyl chloride