{4-[(S)-2-tert-Butoxycarbonylamino-2-((1S,2S,4R)-1-cyclohexylmethyl-2,4-dihydroxy-hexylcarbamoyl)-ethyl]-thiazol-2-yl}-carbamic acid benzyl ester

Base Information

• Chemical Name: {4-[(S)-2-tert-Butoxycarbonylamino-2-((1S,2S,4R)-1-cyclohexylmethyl-2,4-dihydroxy-hexylcarbamoyl)-ethyl]-thiazol-2-yl}-carbamic acid benzyl ester
• CAS No.: 142103-57-9
• Molecular Formula: C₃₂H₄₈N₄O₇S
• Molecular Weight: 632.822

Synonyms:{4-[(S)-2-tert-Butoxycarbonylamino-2-((1S,2S,4R)-1-cyclohexylmethyl-2,4-dihydroxy-hexylcarbamoyl)-ethyl]-thiazol-2-yl}-carbamic acid benzyl ester

Chemical Property of {4-[(S)-2-tert-Butoxycarbonylamino-2-((1S,2S,4R)-1-cyclohexylmethyl-2,4-dihydroxy-hexylcarbamoyl)-ethyl]-thiazol-2-yl}-carbamic acid benzyl ester

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Technology Process of {4-[(S)-2-tert-Butoxycarbonylamino-2-((1S,2S,4R)-1-cyclohexylmethyl-2,4-dihydroxy-hexylcarbamoyl)-ethyl]-thiazol-2-yl}-carbamic acid benzyl ester

There total 4 articles about {4-[(S)-2-tert-Butoxycarbonylamino-2-((1S,2S,4R)-1-cyclohexylmethyl-2,4-dihydroxy-hexylcarbamoyl)-ethyl]-thiazol-2-yl}-carbamic acid benzyl ester 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: 33.0%

<2S-(2R*,3R*,5S*)>-2-amino-1-cyclohexyl-3,5-heptanediol (131099-30-4) + N-<(1,1-dimethylethoxy)carbonyl>-3-<2-<<(phenylmethoxy)carbonyl>amino>-4-thiazolyl>-L-alanine (135704-24-4) → {4-[(S)-2-tert-Butoxycarbonylamino-2-((1S,2S,4R)-1-cyclohexylmethyl-2,4-dihydroxy-hexylcarbamoyl)-ethyl]-thiazol-2-yl}-carbamic acid benzyl ester (142103-57-9)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/jm00092a006

Reference yield:

(S)-3-(2-Amino-thiazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid benzyl ester (135704-30-2) → {4-[(S)-2-tert-Butoxycarbonylamino-2-((1S,2S,4R)-1-cyclohexylmethyl-2,4-dihydroxy-hexylcarbamoyl)-ethyl]-thiazol-2-yl}-carbamic acid benzyl ester (142103-57-9)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. sodium bicarbonate / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

2: 80 percent / aq. KOH / ethanol / 4 h / Ambient temperature

3: 33 percent / N-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC) / dimethylformamide / 0 - 20 °C

With potassium hydroxide; sodium hydrogencarbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00092a006

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → {4-[(S)-2-tert-Butoxycarbonylamino-2-((1S,2S,4R)-1-cyclohexylmethyl-2,4-dihydroxy-hexylcarbamoyl)-ethyl]-thiazol-2-yl}-carbamic acid benzyl ester (142103-57-9)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. sodium bicarbonate / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

2: 80 percent / aq. KOH / ethanol / 4 h / Ambient temperature

3: 33 percent / N-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC) / dimethylformamide / 0 - 20 °C

With potassium hydroxide; sodium hydrogencarbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00092a006

upstream raw materials:

<2S-(2R*,3R*,5S*)>-2-amino-1-cyclohexyl-3,5-heptanediol

N-<(1,1-dimethylethoxy)carbonyl>-3-<2-<<(phenylmethoxy)carbonyl>amino>-4-thiazolyl>-L-alanine

(S)-3-(2-Amino-thiazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid benzyl ester

benzyl chloroformate

Downstream raw materials:

(4-{(S)-2-((1S,2S,4R)-1-Cyclohexylmethyl-2,4-dihydroxy-hexylcarbamoyl)-2-[(S)-2-(morpholine-4-sulfonylamino)-3-phenyl-propionylamino]-ethyl}-thiazol-2-yl)-carbamic acid benzyl ester

<1S-(1R*,2R*,4S*)>-N-(4-morpholinylsulfonyl)-L-phenylalanyl-3-(2-amino-4-thiazolyl)-N-<1-(cyclohexylmethyl)-2,4-dihydroxyhexyl>-L-alaninamide

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