(S)-3-(4-Benzyloxy-phenyl)-2-(2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-propionic acid

Base Information

• Chemical Name: (S)-3-(4-Benzyloxy-phenyl)-2-(2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-propionic acid
• CAS No.: 123168-13-8
• Molecular Formula: C₃₉H₄₃NO₇S
• Molecular Weight: 669.839

Synonyms:(S)-3-(4-Benzyloxy-phenyl)-2-(2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-propionic acid

Chemical Property of (S)-3-(4-Benzyloxy-phenyl)-2-(2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-propionic acid

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Technology Process of (S)-3-(4-Benzyloxy-phenyl)-2-(2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-propionic acid

There total 9 articles about (S)-3-(4-Benzyloxy-phenyl)-2-(2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-propionic acid 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: 40.0%

C23H27ClO4S (93962-31-3) + O-benzyltyrosine hydrochloride (123168-08-1) → (S)-3-(4-Benzyloxy-phenyl)-2-(2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-propionic acid (123168-13-8)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1021/jo00286a019

Reference yield:

diphenyl sulfide (139-66-2) → (S)-3-(4-Benzyloxy-phenyl)-2-(2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-propionic acid (123168-13-8)

Guidance literature:

Multi-step reaction with 6 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: 40 percent / 10percent aq. Na₂CO₃ / tetrahydrofuran / 2 h / 0 °C

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

DOI:10.1021/jo00286a019

Reference yield:

bis(4-tert-butylphenyl) sulfide (52908-55-1) → (S)-3-(4-Benzyloxy-phenyl)-2-(2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-propionic acid (123168-13-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 37 percent / tin(IV) chloride / CH₂Cl₂ / 12 h / Ambient temperature

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

3: 55 percent / 30percent H₂O₂, acetic acid / 4 h / 100 °C

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

5: 40 percent / 10percent aq. Na₂CO₃ / tetrahydrofuran / 2 h / 0 °C

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

DOI:10.1021/jo00286a019

upstream raw materials:

C₂₃H₂₇ClO₄S

O-benzyltyrosine hydrochloride

thioxanthene

diphenyl sulfide

Downstream raw materials:

[(S)-2-(4-Benzyloxy-phenyl)-1-chlorocarbonyl-ethyl]-carbamic acid 2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethyl ester

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

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