L-Serine, O-(1,1-dimethyl-2-propenyl)-N-[(2,2,2-trichloro-1,1-dimethylethoxy)carb onyl]-L-seryl-L-isoleucyl-L-alanyl-L-prolylthio-L-phenylalanyl-, methyl ester

Base Information

• Chemical Name: L-Serine, O-(1,1-dimethyl-2-propenyl)-N-[(2,2,2-trichloro-1,1-dimethylethoxy)carb onyl]-L-seryl-L-isoleucyl-L-alanyl-L-prolylthio-L-phenylalanyl-, methyl ester
• CAS No.: 340270-75-9
• Molecular Formula: C40H59Cl3N6O10S
• Molecular Weight: 922.368
• Mol file: 340270-75-9.mol

Synonyms:

Chemical Property of L-Serine, O-(1,1-dimethyl-2-propenyl)-N-[(2,2,2-trichloro-1,1-dimethylethoxy)carb onyl]-L-seryl-L-isoleucyl-L-alanyl-L-prolylthio-L-phenylalanyl-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Serine, O-(1,1-dimethyl-2-propenyl)-N-[(2,2,2-trichloro-1,1-dimethylethoxy)carb onyl]-L-seryl-L-isoleucyl-L-alanyl-L-prolylthio-L-phenylalanyl-, methyl ester

There total 14 articles about L-Serine, O-(1,1-dimethyl-2-propenyl)-N-[(2,2,2-trichloro-1,1-dimethylethoxy)carb onyl]-L-seryl-L-isoleucyl-L-alanyl-L-prolylthio-L-phenylalanyl-, methyl 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: 72.0%

(S)-3-(1,1-Dimethyl-allyloxy)-2-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-propionic acid (340270-70-4) + (S)-2-[(S)-2-({(S)-1-[(S)-2-((2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-thiopropionylamino]-3-hydroxy-propionic acid methyl ester (340270-74-8) → 2-(2-{[1-(2-{2-[3-(1,1-dimethyl-allyloxy)-2-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-propionylamino]-3-methyl-pentanoylamino}-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-phenyl-thiopropionylamino)-3-hydroxy-propionic acid methyl ester (340270-75-9)

Guidance literature:

(S)-2-[(S)-2-({(S)-1-[(S)-2-((2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-thiopropionylamino]-3-hydroxy-propionic acid methyl ester; With acetyl chloride; In methanol;

(S)-3-(1,1-Dimethyl-allyloxy)-2-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-propionic acid; With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/S0040-4039(01)00194-0

Reference yield:

(S)-3-(1,1-Dimethyl-allyloxy)-2-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-propionic acid (340270-70-4) + (S)-2-[(S)-2-({(S)-1-[(S)-2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-thiopropionylamino]-3-hydroxy-propionic acid methyl ester; hydrochloride → 2-(2-{[1-(2-{2-[3-(1,1-dimethyl-allyloxy)-2-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-propionylamino]-3-methyl-pentanoylamino}-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-phenyl-thiopropionylamino)-3-hydroxy-propionic acid methyl ester (340270-75-9)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 23h;

DOI:10.1016/S0040-4020(03)00294-1

Reference yield:

(S)-methyl 2-((2S)-2-[(tert-butoxycarbonyl)-3-phenylpropanamido]-3-hydroxy)-propanoate (34290-59-0) → 2-(2-{[1-(2-{2-[3-(1,1-dimethyl-allyloxy)-2-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-propionylamino]-3-methyl-pentanoylamino}-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-phenyl-thiopropionylamino)-3-hydroxy-propionic acid methyl ester (340270-75-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 90 percent / imidazole / dimethylformamide / 3 h / 20 °C

2: 92 percent / Lawesson's reagent / benzene / 2 h / Heating

3: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 20 °C

4: acetyl chloride / methanol / 3 h / 20 °C

5: diisopropylethylamine; HOBt; DCC / CH₂Cl₂ / 63 h / 0 - 20 °C

6: acetyl chloride / methanol / 7 h / 20 °C

7: 1.85 g / diisopropylethylamine; HOBt; DCC / CH₂Cl₂ / 24 h / 0 - 20 °C

8: acetyl chloride / methanol / 11 h / 20 °C

9: 80 percent / diisopropylethylamine; HOBt; DCC / CH₂Cl₂ / 51 h / 0 - 20 °C

10: acetyl chloride / methanol / 3.5 h / 20 °C

11: 249 mg / diisopropylethylamine; HOBt; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 23 h / 0 - 20 °C

With Lawessons reagent; 1H-imidazole; tetrabutyl ammonium fluoride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; acetyl chloride; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(03)00294-1

upstream raw materials:

(S)-3-(1,1-Dimethyl-allyloxy)-2-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-propionic acid

(S)-2-[(S)-2-({(S)-1-[(S)-2-((2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-thiopropionylamino]-3-hydroxy-propionic acid methyl ester

N-tert-butoxycarbonyl-L-phenylalanine

(S)-methyl 2-((2S)-2-[(tert-butoxycarbonyl)-3-phenylpropanamido]-3-hydroxy)-propanoate

Downstream raw materials:

(S)-2-((S)-2-{[(S)-1-((S)-2-{(2S,3S)-2-[(S)-2-Amino-3-(1,1-dimethyl-allyloxy)-propionylamino]-3-methyl-pentanoylamino}-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-phenyl-thiopropionylamino)-3-hydroxy-propionic acid methyl ester

C₄₉H₇₂Cl₃N₇O₁₁S

C₄₉H₇₄Cl₃N₇O₁₂S