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

Base Information

• Chemical Name: (R^*)-N-<1-(cyclohexylmethyl)-2,3-dioxohexyl>-N²-<(1,1-dimethylethoxy)carbonyl>-1-<(4-methylphenyl)sulfonyl>-L-histidinamide
• CAS No.: 120915-58-4
• Molecular Formula: C₃₁H₄₄N₄O₇S
• Molecular Weight: 616.779

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

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

Chemical Property:

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

There total 8 articles about (R^*)-N-<1-(cyclohexylmethyl)-2,3-dioxohexyl>-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: 96.0%

(S*,R*)-N-<1-(cyclohexylmethyl)-2-hydroxy-3-oxohexyl>-N2-<(1,1-dimethylethoxy)carbonyl>-1-<(4-methylphenyl)sulfonyl>-L-histidinamide (151593-69-0) → (R*)-N-<1-(cyclohexylmethyl)-2,3-dioxohexyl>-N2-<(1,1-dimethylethoxy)carbonyl>-1-<(4-methylphenyl)sulfonyl>-L-histidinamide (120915-58-4)

Guidance literature:

With Dess-Martin periodane; tert-butyl alcohol; In dichloromethane; for 2h;

DOI:10.1021/jm00069a001

Reference yield:

N-(tert-butoxycarbonyl)-L-histidine (17791-52-5) → (R*)-N-<1-(cyclohexylmethyl)-2,3-dioxohexyl>-N2-<(1,1-dimethylethoxy)carbonyl>-1-<(4-methylphenyl)sulfonyl>-L-histidinamide (120915-58-4)

Guidance literature:

Multi-step reaction with 5 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

4: 67.9 percent / Tl(NO₃)3*H₂O / methanol; diethyl ether / 15 h / 0 °C

5: 96 percent / Dess-Martin periodinane reagent, tBuOH / CH₂Cl₂ / 2 h

With diphenylphosphoranyl azide; sodium carbonate; Dess-Martin periodane; triethylamine; thallium(III) nitrate; tert-butyl alcohol; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; water;

DOI:10.1021/jm00069a001

Reference yield:

(S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid (37736-82-6) → (R*)-N-<1-(cyclohexylmethyl)-2,3-dioxohexyl>-N2-<(1,1-dimethylethoxy)carbonyl>-1-<(4-methylphenyl)sulfonyl>-L-histidinamide (120915-58-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) 1,1'-carbonyldiimidazole, 2.) triethylamine / 1.) THF, 0 deg C, 30 min, 2.) THF, RT, 2.5 h

2: 85.8 percent / LiAlH₄ / tetrahydrofuran; diethyl ether / 0.5 h / 0 - 2 °C

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

4: 75 percent / HCl in EtOAc / 1.) 0 deg C, 1 h, 2.) RT, 3 h

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

6: 98 percent / triethylamine / dioxane / 0.25 h

7: 67.9 percent / Tl(NO₃)3*H₂O / methanol; diethyl ether / 15 h / 0 °C

8: 96 percent / Dess-Martin periodinane reagent, tBuOH / CH₂Cl₂ / 2 h

With hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; diphenylphosphoranyl azide; Dess-Martin periodane; triethylamine; 1,1'-carbonyldiimidazole; thallium(III) nitrate; tert-butyl alcohol; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jm00069a001

upstream raw materials:

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

(S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid

(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal

(S)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-N-methoxy-N-methylcyclohexanepropanamide

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