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

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
• CAS No.: 93962-32-4
• Molecular Formula: C₃₂H₃₇NO₆S
• Molecular Weight: 563.715

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

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

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

There total 11 articles about (S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-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: 72.0%

(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) → (S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid (93962-32-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; Ambient temperature;

DOI:10.1021/jo00286a019

Reference yield: 70.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + C23H27ClO4S (93962-31-3) → (S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionic acid (93962-32-4)

Guidance literature:

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

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 (93962-32-4)

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: 70 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

upstream raw materials:

L-phenylalanine

C₂₃H₂₇ClO₄S

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

thioxanthene

Downstream raw materials:

(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

((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

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