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

Base Information

• Chemical Name: (S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid tert-butyl ester
• CAS No.: 123168-09-2
• Molecular Formula: C₃₆H₄₅NO₆S
• Molecular Weight: 619.822

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

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

Chemical Property:

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

There total 9 articles about (S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionic 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: 77.0%

C23H27ClO4S (93962-31-3) + L-phenylalanine tert-butyl ester hydrochloride (15100-75-1,75898-47-4) → (S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid tert-butyl ester (123168-09-2)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; at 0 ℃; for 0.333333h;

DOI:10.1021/jo00286a019

Reference yield:

diphenyl sulfide (139-66-2) → (S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid tert-butyl ester (123168-09-2)

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: 77 percent / 10percent aq. NaHCO₃ / tetrahydrofuran / 0.33 h / 0 °C

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

DOI:10.1021/jo00286a019

Reference yield:

bis(4-tert-butylphenyl) sulfide (52908-55-1) → (S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid tert-butyl ester (123168-09-2)

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: 77 percent / 10percent aq. NaHCO₃ / tetrahydrofuran / 0.33 h / 0 °C

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

DOI:10.1021/jo00286a019

upstream raw materials:

C₂₃H₂₇ClO₄S

L-phenylalanine tert-butyl ester hydrochloride

thioxanthene

diphenyl sulfide

Downstream raw materials:

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

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

(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 methyl ester

(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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