5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-7-deoxy-13-[[(4S,5R)-2-(4-methoxyphenyl)-3-(tert-butyloxycarbonyl)-4-phenyl-1,3-oxazolidin-5-yl]carbonyl]baccatin III

Base Information

• Chemical Name: 5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-7-deoxy-13-[[(4S,5R)-2-(4-methoxyphenyl)-3-(tert-butyloxycarbonyl)-4-phenyl-1,3-oxazolidin-5-yl]carbonyl]baccatin III
• CAS No.: 1054734-45-0
• Molecular Formula: C₅₃H₆₁NO₁₄S
• Molecular Weight: 968.132

Synonyms:5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-7-deoxy-13-[[(4S,5R)-2-(4-methoxyphenyl)-3-(tert-butyloxycarbonyl)-4-phenyl-1,3-oxazolidin-5-yl]carbonyl]baccatin III

Chemical Property of 5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-7-deoxy-13-[[(4S,5R)-2-(4-methoxyphenyl)-3-(tert-butyloxycarbonyl)-4-phenyl-1,3-oxazolidin-5-yl]carbonyl]baccatin III

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Technology Process of 5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-7-deoxy-13-[[(4S,5R)-2-(4-methoxyphenyl)-3-(tert-butyloxycarbonyl)-4-phenyl-1,3-oxazolidin-5-yl]carbonyl]baccatin III

There total 7 articles about 5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-7-deoxy-13-[[(4S,5R)-2-(4-methoxyphenyl)-3-(tert-butyloxycarbonyl)-4-phenyl-1,3-oxazolidin-5-yl]carbonyl]baccatin III 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: 78.0%

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + 7-deoxy-5(20)-deoxy-5(20)-sulfanylbaccatin III (358621-71-3) → 5(20)-deoxy-5(20)-sulfanyl-7-deoxy-13-[[(4S,5R)-2-(4-methoxyphenyl)-3-(tert-butyloxycarbonyl)-4-phenyl-1,3-oxazolidin-5-yl]carbonyl]baccatin III (1054734-45-0)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In toluene; at 80 ℃; for 3h;

DOI:10.1021/jo015539+

Reference yield:

1,2-O-benzylidene-9-oxo-10-acetyltaxicine I → 5(20)-deoxy-5(20)-sulfanyl-7-deoxy-13-[[(4S,5R)-2-(4-methoxyphenyl)-3-(tert-butyloxycarbonyl)-4-phenyl-1,3-oxazolidin-5-yl]carbonyl]baccatin III (1054734-45-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / 0 °C

2: 73 percent / pyridine / 0.5 h / 0 °C

3: 56 percent / CuCl₂; tBuOOH / toluene / 504000 h / 20 °C

4: 12 percent / dimethylformamide / 17 h / 60 °C

5: 60 percent / sodium borohydride / tetrahydrofuran; methanol / 2 h / 0 °C

6: 78 percent / 4-(dimethylamino)pyridine; 1,3-dicyclohexylcarbodiimide / toluene / 3 h / 80 °C

With pyridine; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; copper dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo015539+

Reference yield:

1,2-O-benzylidene-9-oxo-10-acetyl-4α(20)-epoxy-5-mesyltaxicine I (1027565-02-1) → 5(20)-deoxy-5(20)-sulfanyl-7-deoxy-13-[[(4S,5R)-2-(4-methoxyphenyl)-3-(tert-butyloxycarbonyl)-4-phenyl-1,3-oxazolidin-5-yl]carbonyl]baccatin III (1054734-45-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 56 percent / CuCl₂; tBuOOH / toluene / 504000 h / 20 °C

2: 12 percent / dimethylformamide / 17 h / 60 °C

3: 60 percent / sodium borohydride / tetrahydrofuran; methanol / 2 h / 0 °C

4: 78 percent / 4-(dimethylamino)pyridine; 1,3-dicyclohexylcarbodiimide / toluene / 3 h / 80 °C

With tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; dicyclohexyl-carbodiimide; copper dichloride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo015539+

upstream raw materials:

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

7-deoxy-5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanylbaccatin III

1,2-O-benzylidene-9-oxo-10-acetyl-4α(20)-epoxytaxicine I

1,2-O-benzylidene-9-oxo-10-acetyl-4α(20)-epoxy-5-mesyltaxicine I

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