(S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester

Base Information

• Chemical Name: (S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester
• CAS No.: 93962-34-6
• Molecular Formula: C₄₂H₅₆N₂O₇S
• Molecular Weight: 732.982

Synonyms:(S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester

Chemical Property of (S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester

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Technology Process of (S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester

There total 13 articles about (S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic 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: 71.0%

L-leucine tert-butyl ester hydrochloride (2748-02-9,13081-32-8) + ((S)-1-Chlorocarbonyl-2-phenyl-ethyl)-carbamic acid 2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethyl ester (123168-15-0) → (S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester (93962-34-6)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/jo00286a019

Reference yield: 51.0%

L-leucine tert-butyl ester (21691-53-2) + (S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid (93962-32-4) → (S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester (93962-34-6)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; 1.) -15 deg C, 1 h, 2.) room temperature, 2 h;

DOI:10.1021/jo00286a019

Reference yield:

diphenyl sulfide (139-66-2) → (S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester (93962-34-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / ferric chloride / CH₂Cl₂ / 72 h / Heating

2: 37 percent / tin(IV) chloride / CH₂Cl₂ / 12 h / Ambient temperature

3: 1.) n-butyllithium / 1.) THF, -75 deg C, 30 min, 2.) reflux, 30 min

4: 55 percent / 30percent H₂O₂, acetic acid / 4 h / 100 °C

5: 87 percent / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) room temperature, 4 h

6: 70 percent / 10percent aq. Na₂CO₃ / tetrahydrofuran / 2 h / 0 °C

7: 51 percent / dicyclohexylcarbodiimide (DCC) / tetrahydrofuran / 1.) -15 deg C, 1 h, 2.) room temperature, 2 h

With n-butyllithium; dihydrogen peroxide; iron(III) chloride; tin(IV) chloride; sodium carbonate; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00286a019

upstream raw materials:

L-leucine tert-butyl ester

(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid

L-leucine tert-butyl ester hydrochloride

((S)-1-Chlorocarbonyl-2-phenyl-ethyl)-carbamic acid 2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethyl ester

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