(1R,2R)-2-Methanesulfonylamino-cyclohexanecarbothioic acid [(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-amide

Base Information

• Chemical Name: (1R,2R)-2-Methanesulfonylamino-cyclohexanecarbothioic acid [(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-amide
• CAS No.: 423760-37-6
• Molecular Formula: C₁₉H₄₀N₂O₃S₂Si
• Molecular Weight: 436.756
• Mol file: 423760-37-6.mol

Synonyms:(1R,2R)-2-Methanesulfonylamino-cyclohexanecarbothioic acid [(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-amide

Chemical Property of (1R,2R)-2-Methanesulfonylamino-cyclohexanecarbothioic acid [(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-2-Methanesulfonylamino-cyclohexanecarbothioic acid [(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-amide

There total 8 articles about (1R,2R)-2-Methanesulfonylamino-cyclohexanecarbothioic acid [(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-amide 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: 65.0%

(1R,2R)-2-Methanesulfonylamino-cyclohexanecarboxylic acid [(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-amide (423760-35-4) → (1R,2R)-2-Methanesulfonylamino-cyclohexanecarbothioic acid [(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-amide (423760-37-6)

Guidance literature:

With Lawessons reagent; In dichloromethane; at 20 ℃; for 23h;

DOI:10.1021/ol025600c

Reference yield:

(1R,6R)-6-(2-oxo-oxazolidine-3-carbonyl)-cyclohex-3-ene carboxylic acid methyl ester (116733-43-8) → (1R,2R)-2-Methanesulfonylamino-cyclohexanecarbothioic acid [(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-amide (423760-37-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 98 percent / LiOH*H₂O; H₂O₂ / tetrahydrofuran; H₂O / 19 h / 20 °C

2.1: diphenylphosphoryl azide; Et₃N / toluene / 3 h / 20 °C

2.2: 1.15 g / toluene / 13.5 h / 85 °C

3.1: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

4.1: 250 mg / Et₃N / CH₂Cl₂ / 19 h / 20 °C

5.1: 183 mg / LiOH*H₂O / tetrahydrofuran; H₂O / 19 h / 20 °C

6.1: (COCl)2 / CH₂Cl₂; dimethylformamide / 20 h / 20 °C

7.1: 226 mg / Et₃N / CH₂Cl₂ / 3.5 h / 20 °C

8.1: 96 percent / imidazole / dimethylformamide / 5 h / 0 °C

9.1: 65 percent / Lawesson's reagent / CH₂Cl₂ / 23 h / 20 °C

With Lawessons reagent; 1H-imidazole; lithium hydroxide; oxalyl dichloride; diphenylphosphoranyl azide; hydrogen; dihydrogen peroxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol025600c

Reference yield:

(1R,6R)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester (91280-45-4) → (1R,2R)-2-Methanesulfonylamino-cyclohexanecarbothioic acid [(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-amide (423760-37-6)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

2: 250 mg / Et₃N / CH₂Cl₂ / 19 h / 20 °C

3: 183 mg / LiOH*H₂O / tetrahydrofuran; H₂O / 19 h / 20 °C

4: (COCl)2 / CH₂Cl₂; dimethylformamide / 20 h / 20 °C

5: 226 mg / Et₃N / CH₂Cl₂ / 3.5 h / 20 °C

6: 96 percent / imidazole / dimethylformamide / 5 h / 0 °C

7: 65 percent / Lawesson's reagent / CH₂Cl₂ / 23 h / 20 °C

With Lawessons reagent; 1H-imidazole; lithium hydroxide; oxalyl dichloride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ol025600c

upstream raw materials:

(1R,2R)-2-Methanesulfonylamino-cyclohexanecarboxylic acid [(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-amide

(1R,2R)-2-aminocyclohexanecarboxylic acid methyl ester

(1R,6R)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester

(1R,6R)-6-(2-oxo-oxazolidine-3-carbonyl)-cyclohex-3-ene carboxylic acid methyl ester