7,10-di(2,2,2-trichloroethyloxy-carbonyl)-13-cinnamoyl-10-deacetyl baccatin III

Base Information

• Chemical Name: 7,10-di(2,2,2-trichloroethyloxy-carbonyl)-13-cinnamoyl-10-deacetyl baccatin III
• CAS No.: 95603-45-5
• Molecular Formula: C₄₄H₄₄Cl₆O₁₅
• Molecular Weight: 1025.54
• Mol file: 95603-45-5.mol

Synonyms:

Chemical Property of 7,10-di(2,2,2-trichloroethyloxy-carbonyl)-13-cinnamoyl-10-deacetyl baccatin III

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7,10-di(2,2,2-trichloroethyloxy-carbonyl)-13-cinnamoyl-10-deacetyl baccatin III

There total 2 articles about 7,10-di(2,2,2-trichloroethyloxy-carbonyl)-13-cinnamoyl-10-deacetyl 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: 94.0%

(E)-3-phenylacrylic acid (140-10-3) + 7,10-di-(2,2,2-trichloroethyloxycarbonyl)-10-deacetylbaccatin III (95603-44-4) → 7,10-di(2,2,2-trichloroethyloxy-carbonyl)-13-cinnamoyl-10-deacetyl baccatin III (95603-45-5,110281-75-9)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; at 70 ℃; for 15h;

DOI:10.1016/S0040-4020(01)81313-2

Reference yield:

10-deacetylbaccatin III (32981-86-5,172018-16-5) → 7,10-di(2,2,2-trichloroethyloxy-carbonyl)-13-cinnamoyl-10-deacetyl baccatin III (95603-45-5,110281-75-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 153 mg / pyridine / 0.08 h / 80 °C

2: 42 mg / 1.) oxalyl chloride; 2.) silver cyanide / toluene / 20 h / 110 °C

With silver cyanide; oxalyl dichloride; In pyridine; toluene;

DOI:10.1016/S0040-4020(01)87285-9

Reference yield:

7,10-di(2,2,2-trichloroethyloxy-carbonyl)-13-cinnamoyl-10-deacetyl baccatin III (95603-45-5,110281-75-9) → 10-deacetyltaxol (78432-77-6,78454-17-8,125354-13-4,133577-34-1,133577-35-2,135501-18-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.92 g / m-chloroperbenzoic acid, sodium carbonate / CH₂Cl₂ / 22 h / 20 °C

2: 570 mg / sodium azide, ammonium chloride / ethanol / 15 h / Heating

3: acetic acid, zinc dust / 1 h / 60 °C

4: pyridine / 0.17 h / Ambient temperature

With pyridine; sodium azide; ammonium chloride; sodium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; zinc; In ethanol; dichloromethane;

DOI:10.1021/jm00107a017

upstream raw materials:

(E)-3-phenylacrylic acid

7,10-di-(2,2,2-trichloroethyloxycarbonyl)-10-deacetylbaccatin III

10-deacetylbaccatin III

Downstream raw materials:

13-cynnamoyl-10-deacetyl baccatin III

C₄₄H₄₆Cl₆O₁₇

13-hydroxy acetyl-10-deacetyl baccatin III

C₃₇H₃₈Cl₆O₁₆

Refernces

• 1、 Gueritte-Voegelein, F.,Senilh, V.,David, B.,Guenard, B.,Potier, P.. "CHEMICAL STUDIES OF 10-DEACETYL BACCATIN III. HEMISYNTHESIS OF TAXOL DERIVATIVES.". . p. 4451 - 4460. Retrieved 2007/10/02.