(S)-8-[(R)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-2-methyl-propionylamino]-8-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyloxycarbonyl-ethylcarbamoyl]-octanoic acid tert-butyl ester

Base Information

Chemical Name:(S)-8-[(R)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-2-methyl-propionylamino]-8-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyloxycarbonyl-ethylcarbamoyl]-octanoic acid tert-butyl ester
CAS No.:187396-04-9
Molecular Formula:C₄₉H₇₀N₆O₁₀
Molecular Weight:903.129
Hs Code.:

(S)-8-[(R)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-2-methyl-propionylamino]-8-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyloxycarbonyl-ethylcarbamoyl]-octanoic acid tert-butyl ester

Synonyms:(S)-8-[(R)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-2-methyl-propionylamino]-8-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyloxycarbonyl-ethylcarbamoyl]-octanoic acid tert-butyl ester

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Chemical Property of (S)-8-[(R)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-2-methyl-propionylamino]-8-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyloxycarbonyl-ethylcarbamoyl]-octanoic acid tert-butyl ester

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Technology Process of (S)-8-[(R)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-2-methyl-propionylamino]-8-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyloxycarbonyl-ethylcarbamoyl]-octanoic acid tert-butyl ester

There total 6 articles about (S)-8-[(R)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-2-methyl-propionylamino]-8-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyloxycarbonyl-ethylcarbamoyl]-octanoic acid tert-butyl 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:

: 51100-47-1
7-bromoheptanoic acid t-butyl ester

: 187396-04-9
(S)-8-[(R)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-2-methyl-propionylamino]-8-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyloxycarbonyl-ethylcarbamoyl]-octanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -55 deg C, b) RT, 16 h

2: 10percent aq. citric acid / tetrahydrofuran / 48 h / Ambient temperature

3: Et₃N / tetrahydrofuran / 2 h / Ambient temperature

4: 50 percent / 0.5 N aq. LiOH / tetrahydrofuran / 4 h / Ambient temperature

5: 1.) DIEA, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, 2.) DIEA / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, overnight

6: 100 percent / H₂ / 10percent Pd/C / methanol / Ambient temperature

7: 1.) DIEA, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, 2.) DIEA / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, overnight

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; n-butyllithium; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; citric acid; palladium on activated charcoal; In tetrahydrofuran; methanol;
DOI:10.1021/jm9603072

Reference yield:

: 187395-95-5
(S)-2-Benzyloxycarbonylamino-nonanedioic acid 9-tert-butyl ester

: 187396-04-9
(S)-8-[(R)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-2-methyl-propionylamino]-8-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyloxycarbonyl-ethylcarbamoyl]-octanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) DIEA, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, 2.) DIEA / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, overnight

2: 100 percent / H₂ / 10percent Pd/C / methanol / Ambient temperature

3: 1.) DIEA, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, 2.) DIEA / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, overnight

With hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol;
DOI:10.1021/jm9603072

Reference yield:

: 1026573-49-8
(S)-8-Amino-9-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-9-oxo-nonanoic acid tert-butyl ester

: 187396-04-9
(S)-8-[(R)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-2-methyl-propionylamino]-8-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyloxycarbonyl-ethylcarbamoyl]-octanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N / tetrahydrofuran / 2 h / Ambient temperature

2: 50 percent / 0.5 N aq. LiOH / tetrahydrofuran / 4 h / Ambient temperature

3: 1.) DIEA, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, 2.) DIEA / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, overnight

4: 100 percent / H₂ / 10percent Pd/C / methanol / Ambient temperature

5: 1.) DIEA, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, 2.) DIEA / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, overnight

With lithium hydroxide; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol;
DOI:10.1021/jm9603072