Benzyl (R)-3-(2-benzyloxycarbonylaminoethylsulfanyl)-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1⁽¹⁷⁾,14⁽¹⁸⁾,15-trien-12-yl)ureido]propionate

Base Information

• Chemical Name: Benzyl (R)-3-(2-benzyloxycarbonylaminoethylsulfanyl)-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1⁽¹⁷⁾,14⁽¹⁸⁾,15-trien-12-yl)ureido]propionate
• CAS No.: 1198185-68-0
• Molecular Formula: C₃₉H₅₀N₄O₈S
• Molecular Weight: 734.914

Synonyms:Benzyl (R)-3-(2-benzyloxycarbonylaminoethylsulfanyl)-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1⁽¹⁷⁾,14⁽¹⁸⁾,15-trien-12-yl)ureido]propionate

Chemical Property of Benzyl (R)-3-(2-benzyloxycarbonylaminoethylsulfanyl)-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1⁽¹⁷⁾,14⁽¹⁸⁾,15-trien-12-yl)ureido]propionate

Chemical Property:

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Technology Process of Benzyl (R)-3-(2-benzyloxycarbonylaminoethylsulfanyl)-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1⁽¹⁷⁾,14⁽¹⁸⁾,15-trien-12-yl)ureido]propionate

There total 10 articles about Benzyl (R)-3-(2-benzyloxycarbonylaminoethylsulfanyl)-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1⁽¹⁷⁾,14⁽¹⁸⁾,15-trien-12-yl)ureido]propionate 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:

(9S,12R)-12-amino-9-isopropyl-2,7-dioxa-1O-aza-bicyclo[12.2.2]octadeca-1(17),14(18),15-trien-11-one (1198185-28-2) + Benzyl (R)-2-amino-3-(2-benzyloxycarbonylaminoethylsulfanyl)propionate (732211-08-4) + 1,1'-carbonyldiimidazole (530-62-1) → Benzyl (R)-3-(2-benzyloxycarbonylaminoethylsulfanyl)-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-yl)ureido]propionate (1198185-68-0)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

Reference yield:

9H-fluoren-9-ylmethyl [(R)-1-[(S)-(1-allyloxymethyl-2-methylpropylcarbamoyl)]-2-(4-allyloxyphenyl)ethyl]carbamate (1198185-26-0) → Benzyl (R)-3-(2-benzyloxycarbonylaminoethylsulfanyl)-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-yl)ureido]propionate (1198185-68-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Hoveyda-Grubbs catalyst first generation / dichloromethane / 24 h / 40 °C

2: hydrogen / palladium 10% on activated carbon / methanol / 6 h / 21 - 24 °C

3: triethylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With hydrogen; triethylamine; Hoveyda-Grubbs catalyst first generation; palladium 10% on activated carbon; In methanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(S)-valinol (2026-48-4,473-75-6) → Benzyl (R)-3-(2-benzyloxycarbonylaminoethylsulfanyl)-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-yl)ureido]propionate (1198185-68-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: toluene / 1 h / Reflux

2.1: sodium hydride / tetrahydrofuran / 0.75 h / 21 - 24 °C

2.2: 21 - 24 °C

3.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 21 - 24 °C

4.1: Hoveyda-Grubbs catalyst first generation / dichloromethane / 24 h / 40 °C

5.1: hydrogen / palladium 10% on activated carbon / methanol / 6 h / 21 - 24 °C

6.1: triethylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With hydrogen; sodium hydride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; Hoveyda-Grubbs catalyst first generation; palladium 10% on activated carbon; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

(9S,12R)-12-amino-9-isopropyl-2,7-dioxa-1O-aza-bicyclo[12.2.2]octadeca-1⁽¹⁷⁾,14⁽¹⁸⁾,15-trien-11-one

Benzyl (R)-2-amino-3-(2-benzyloxycarbonylaminoethylsulfanyl)propionate

1,1'-carbonyldiimidazole

9H-fluoren-9-ylmethyl [(R)-1-[(S)-(1-allyloxymethyl-2-methylpropylcarbamoyl)]-2-(4-allyloxyphenyl)ethyl]carbamate

Downstream raw materials:

benzyl (R)-3-(2-benzyloxycarbonylaminoethanesulfonyl)-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1⁽¹⁷⁾,14⁽¹⁸⁾,15-trien-12-yl)ureido]propionate

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