7-deoxy-5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-13-oxobaccatin III

Base Information

• Chemical Name: 7-deoxy-5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-13-oxobaccatin III
• CAS No.: 358621-70-2
• Molecular Formula: C₃₁H₃₆O₉S
• Molecular Weight: 584.687
• Mol file: 358621-70-2.mol

Synonyms:

Chemical Property of 7-deoxy-5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-13-oxobaccatin III

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-deoxy-5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-13-oxobaccatin III

There total 5 articles about 7-deoxy-5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-13-oxobaccatin 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: 12.0%

2-benzoyl-9-oxo-10-acetyl-4α(20)-epoxy-5-mesyltaxicine I (358621-69-9) + potassium thioacetate (10387-40-3) → 7-deoxy-5(20)-deoxy-5(20)-sulfanyl-13-oxobaccatin III (358621-70-2)

Guidance literature:

In N,N-dimethyl-formamide; at 60 ℃; for 17h;

DOI:10.1021/jo015539+

Reference yield:

1,2-O-benzylidene-9-oxo-10-acetyl-4α(20)-epoxy-5-mesyltaxicine I (1027565-02-1) → 7-deoxy-5(20)-deoxy-5(20)-sulfanyl-13-oxobaccatin III (358621-70-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With tert.-butylhydroperoxide; copper dichloride; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo015539+

Reference yield:

1,2-O-benzylidene-9-oxo-10-acetyltaxicine I → 7-deoxy-5(20)-deoxy-5(20)-sulfanyl-13-oxobaccatin III (358621-70-2)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; tert.-butylhydroperoxide; 3-chloro-benzenecarboperoxoic acid; copper dichloride; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo015539+

upstream raw materials:

2-benzoyl-9-oxo-10-acetyl-4α(20)-epoxy-5-mesyltaxicine I

potassium thioacetate

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

Downstream raw materials:

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

Refernces