(S)-3-((S)-2-acetamido-3-methylbutanamido)-4-(((S)-1-((2S,3R)-3-cyclohexyl-2-(((2S,3S)-2-hydroxy-5-oxotetrahydrofuran-3-yl)carbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-4-oxobutanoic acid

Base Information

• Chemical Name: (S)-3-((S)-2-acetamido-3-methylbutanamido)-4-(((S)-1-((2S,3R)-3-cyclohexyl-2-(((2S,3S)-2-hydroxy-5-oxotetrahydrofuran-3-yl)carbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-4-oxobutanoic acid
• CAS No.: 1344157-37-4
• Molecular Formula: C₃₁H₄₉N₅O₁₀
• Molecular Weight: 651.758
• Mol file: 1344157-37-4.mol

Synonyms:(S)-3-((S)-2-acetamido-3-methylbutanamido)-4-(((S)-1-((2S,3R)-3-cyclohexyl-2-(((2S,3S)-2-hydroxy-5-oxotetrahydrofuran-3-yl)carbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-4-oxobutanoic acid

Chemical Property of (S)-3-((S)-2-acetamido-3-methylbutanamido)-4-(((S)-1-((2S,3R)-3-cyclohexyl-2-(((2S,3S)-2-hydroxy-5-oxotetrahydrofuran-3-yl)carbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-4-oxobutanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-((S)-2-acetamido-3-methylbutanamido)-4-(((S)-1-((2S,3R)-3-cyclohexyl-2-(((2S,3S)-2-hydroxy-5-oxotetrahydrofuran-3-yl)carbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-4-oxobutanoic acid

There total 11 articles about (S)-3-((S)-2-acetamido-3-methylbutanamido)-4-(((S)-1-((2S,3R)-3-cyclohexyl-2-(((2S,3S)-2-hydroxy-5-oxotetrahydrofuran-3-yl)carbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-4-oxobutanoic acid 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:

cyclohexylmagnesium bromide (931-50-0) → (S)-3-((S)-2-acetamido-3-methylbutanamido)-4-(((S)-1-((2S,3R)-3-cyclohexyl-2-(((2S,3S)-2-hydroxy-5-oxotetrahydrofuran-3-yl)carbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-4-oxobutanoic acid (1344157-37-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: chloro-trimethyl-silane; (methylsulfonyl)methane-bromo copper / 2 h / -78 - 20 °C

2.1: dimethylsulfide borane complex / tetrahydrofuran / 1 h / Reflux

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C

4.1: chromium(VI) oxide; sulfuric acid; water / acetone / 5 h / 20 °C

5.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C

6.1: sodium carbonate / 1,4-dioxane; water / 18 h / 20 °C

7.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 h / 20 °C / solid phase reaction

7.2: 1 h / 20 °C / solid phase reaction

With chromium(VI) oxide; chloro-trimethyl-silane; dimethylsulfide borane complex; sulfuric acid; (methylsulfonyl)methane-bromo copper; tetrabutyl ammonium fluoride; water; sodium carbonate; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.bmc.2011.08.020

Reference yield:

(S)-2-[(S)-2-((S)-2-acetylamino-3-methyl-butyrylamino)-3-tert-butoxycarbonyl-propionylamino]-3-methyl-butyric acid (1344158-52-6) + C17H30N5O4Pol + (2S,3R)-3-cyclohexyl-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester (1344158-31-1) → (S)-3-((S)-2-acetamido-3-methylbutanamido)-4-(((S)-1-((2S,3R)-3-cyclohexyl-2-(((2S,3S)-2-hydroxy-5-oxotetrahydrofuran-3-yl)carbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-4-oxobutanoic acid (1344157-37-4)

Guidance literature:

C₁₇H₃₀N₅O₄Pol; (2S,3R)-3-cyclohexyl-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester; With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃; for 20h; solid phase reaction;

With piperidine; In N,N-dimethyl-formamide; at 20 ℃; for 1h; solid phase reaction;

(S)-2-[(S)-2-((S)-2-acetylamino-3-methyl-butyrylamino)-3-tert-butoxycarbonyl-propionylamino]-3-methyl-butyric acid; Further stages;

DOI:10.1016/j.bmc.2011.08.020

Reference yield:

(2S,3R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-cyclohexyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1344158-12-8) → (S)-3-((S)-2-acetamido-3-methylbutanamido)-4-(((S)-1-((2S,3R)-3-cyclohexyl-2-(((2S,3S)-2-hydroxy-5-oxotetrahydrofuran-3-yl)carbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-4-oxobutanoic acid (1344157-37-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C

2.1: chromium(VI) oxide; sulfuric acid; water / acetone / 5 h / 20 °C

3.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C

4.1: sodium carbonate / 1,4-dioxane; water / 18 h / 20 °C

5.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 h / 20 °C / solid phase reaction

5.2: 1 h / 20 °C / solid phase reaction

With chromium(VI) oxide; sulfuric acid; tetrabutyl ammonium fluoride; water; sodium carbonate; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.bmc.2011.08.020

upstream raw materials:

(S)-2-[(S)-2-((S)-2-acetylamino-3-methyl-butyrylamino)-3-tert-butoxycarbonyl-propionylamino]-3-methyl-butyric acid

(2S,3R)-3-cyclohexyl-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester

(2S,3R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-cyclohexyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,3R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-cyclohexyl-pyrrolidine-1-carboxylic acid tert-butyl ester