(S^*,R^*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-(2-propyl-1,3-dithian-2-yl)ethyl>-N²-<(1,1-dimethylethoxy)carbonyl>-1-<(4-methylphenyl)sulfonyl>-L-histidinamide

Base Information

• Chemical Name: (S^*,R^*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-(2-propyl-1,3-dithian-2-yl)ethyl>-N²-<(1,1-dimethylethoxy)carbonyl>-1-<(4-methylphenyl)sulfonyl>-L-histidinamide
• CAS No.: 151593-68-9
• Molecular Formula: C₃₄H₅₂N₄O₆S₃
• Molecular Weight: 709.008

Synonyms:(S^*,R^*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-(2-propyl-1,3-dithian-2-yl)ethyl>-N²-<(1,1-dimethylethoxy)carbonyl>-1-<(4-methylphenyl)sulfonyl>-L-histidinamide

Chemical Property of (S^*,R^*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-(2-propyl-1,3-dithian-2-yl)ethyl>-N²-<(1,1-dimethylethoxy)carbonyl>-1-<(4-methylphenyl)sulfonyl>-L-histidinamide

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Technology Process of (S^*,R^*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-(2-propyl-1,3-dithian-2-yl)ethyl>-N²-<(1,1-dimethylethoxy)carbonyl>-1-<(4-methylphenyl)sulfonyl>-L-histidinamide

There total 10 articles about (S^*,R^*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-(2-propyl-1,3-dithian-2-yl)ethyl>-N²-<(1,1-dimethylethoxy)carbonyl>-1-<(4-methylphenyl)sulfonyl>-L-histidinamide 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%

p-toluenesulfonyl chloride (98-59-9) + [(S)-1-[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-2-(2-propyl-[1,3]dithian-2-yl)-ethylcarbamoyl]-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester (151521-17-4) → (S*,R*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-(2-propyl-1,3-dithian-2-yl)ethyl>-N2-<(1,1-dimethylethoxy)carbonyl>-1-<(4-methylphenyl)sulfonyl>-L-histidinamide (151593-68-9)

Guidance literature:

With triethylamine; In 1,4-dioxane; for 0.25h;

DOI:10.1021/jm00069a001

Reference yield:

N-(tert-butoxycarbonyl)-L-histidine (17791-52-5) → (S*,R*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-(2-propyl-1,3-dithian-2-yl)ethyl>-N2-<(1,1-dimethylethoxy)carbonyl>-1-<(4-methylphenyl)sulfonyl>-L-histidinamide (151593-68-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 46 percent / Na₂CO₃ / H₂O / 4 h / Ambient temperature

2: 2.) diphenylphosphoryl azide / 1.) CH₂Cl₂, 0 deg C, 5 min, 2.) CH₂Cl₂, a) 0 deg C, 2 h, b) RT, overnight

3: 98 percent / triethylamine / dioxane / 0.25 h

With diphenylphosphoranyl azide; sodium carbonate; triethylamine; In 1,4-dioxane; water;

DOI:10.1021/jm00069a001

Reference yield:

2-(n-propyl)-1,3-dithiane (42196-80-5) → (S*,R*)-N-<1-(cyclohexylmethyl)-2-hydroxy-2-(2-propyl-1,3-dithian-2-yl)ethyl>-N2-<(1,1-dimethylethoxy)carbonyl>-1-<(4-methylphenyl)sulfonyl>-L-histidinamide (151593-68-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) nBuLi / 1.) THF, from -25 to -20 deg C, 2 h, 2.) THF, from -78 to -50 deg C, 18 h

2: 75 percent / HCl in EtOAc / 1.) 0 deg C, 1 h, 2.) RT, 3 h

3: 2.) diphenylphosphoryl azide / 1.) CH₂Cl₂, 0 deg C, 5 min, 2.) CH₂Cl₂, a) 0 deg C, 2 h, b) RT, overnight

4: 98 percent / triethylamine / dioxane / 0.25 h

With hydrogenchloride; n-butyllithium; diphenylphosphoranyl azide; triethylamine; In 1,4-dioxane;

DOI:10.1021/jm00069a001

upstream raw materials:

p-toluenesulfonyl chloride

[(S)-1-[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-2-(2-propyl-[1,3]dithian-2-yl)-ethylcarbamoyl]-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester

Boc-His(Tos)-OH

2-(n-propyl)-1,3-dithiane

Downstream raw materials:

(S^*,R^*)-N-<1-(cyclohexylmethyl)-2-hydroxy-3-oxohexyl>-N²-<(1,1-dimethylethoxy)carbonyl>-1-<(4-methylphenyl)sulfonyl>-L-histidinamide

(R^*)-N-<1-(cyclohexylmethyl)-2,3-dioxohexyl>-N²-<(1,1-dimethylethoxy)carbonyl>-1-<(4-methylphenyl)sulfonyl>-L-histidinamide

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