7-{[(2,2,2,-TRICHLOROETHYL)OXY]CARBONYL} BACCATIN III

Base Information

• Chemical Name: 7-{[(2,2,2,-TRICHLOROETHYL)OXY]CARBONYL} BACCATIN III
• CAS No.: 103150-33-0
• Molecular Formula: C34H39Cl3O13
• Molecular Weight: 762.035
• Mol file: 103150-33-0.mol

Synonyms:7-{[(2,2,2,-TRICHLOROETHYL)OXY]CARBONYL} BACCATIN III;Carbonic acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-9,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-4-yl 2,2,2-trichloroethyl ester;7-O-(2,2,2-Trichloroethoxycarbonyl)baccatin III

Chemical Property of 7-{[(2,2,2,-TRICHLOROETHYL)OXY]CARBONYL} BACCATIN III

Chemical Property:

• Boiling Point: 807.0±65.0 °C(Predicted)
• PKA: 12?+-.0.70(Predicted)
• PSA: 181.19000
• Density: 1.47±0.1 g/cm3(Predicted)
• LogP: 4.18370
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly, Sonicated), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

7-{[(2,2,2,-Trichloroethyl)oxy]carbonyl}BaccatinIII ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 7-{[(2,2,2,-Trichloroethyl)oxy]carbonyl} Baccatin III is a precursor to Paclitaxel (P132500).

Technology Process of 7-{[(2,2,2,-TRICHLOROETHYL)OXY]CARBONYL} BACCATIN III

There total 53 articles about 7-{[(2,2,2,-TRICHLOROETHYL)OXY]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: 87.0%

baccatin III (27548-93-2) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → 7-(2,2,2-trichloroethyloxycarbonyl)baccatin III (103150-33-0)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 3h;

DOI:10.1016/S0040-4020(01)80381-1

Reference yield: 80.0%

C40H53Cl3O13Si (219780-59-3) → 7-(2,2,2-trichloroethyloxycarbonyl)baccatin III (103150-33-0)

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In tetrahydrofuran;

DOI:10.1021/ja9824932

Reference yield:

C26H40O7Si (219780-79-7) → 7-(2,2,2-trichloroethyloxycarbonyl)baccatin III (103150-33-0)

Guidance literature:

Multi-step reaction with 27 steps

1.1: 86 percent / pyridinium p-toluenesulfonate / benzene / 1 h / Heating

2.1: 100 percent / K₂CO₃ / tetrahydrofuran; methanol / 1 h / 20 °C

3.1: 100 percent / SmI₂; methanol / tetrahydrofuran; hexamethylphosphoric acid triamide / 5 h / 20 °C

4.1: TBAF; 2,6-di-t-butyl-4-hydroxytoluene / tetrahydrofuran / 3 h / 20 °C

4.2: 45 percent / sodium methoxide / methanol; tetrahydrofuran / 60 h / 20 °C

5.1: pyridine / CH₂Cl₂ / 0.25 h / 20 °C

6.1: 2,6-lutidine / CH₂Cl₂ / 12 h / -45 °C

7.1: 6.6 mg / aq. hydrogen peroxide; aq. Na₂CO₃ / ethyl acetate / 1 h / 20 °C

8.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

9.1: 97 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 0.08 h / 20 °C

10.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C

10.2: 89 percent / tetrahydrofuran / 1 h / -78 °C

11.1: 91 percent / tetrakis(triphenylphosphine)palladium / diethyl ether; tetrahydrofuran / 1 h / 20 °C

12.1: 88 percent / N-chlorosuccinimide / methanol / 10 h / 20 °C

13.1: 89 percent / pyridinium p-toluenesulfonate; 2-methoxypropene / CH₂Cl₂ / 0.05 h / 20 °C

14.1: 80 percent / lithium diisopropyl amide; MoO₅*pyridine*HMPA / tetrahydrofuran / 0.92 h / -23 °C

15.1: 92 percent / DMAP / CH₂Cl₂ / 0.5 h / 20 °C

16.1: 68 percent / DBN / toluene / 10 h / Heating

17.1: 86 percent / OsO₄; pyridine / diethyl ether; tetrahydrofuran / 18 h / 20 °C

18.1: 86 percent / DBU / toluene / 4 h / Heating

19.1: pyridinium p-toluenesulfonic acid / methanol / 0.5 h / 20 °C

20.1: 15 mg / DMAP; imidazole / dimethylformamide / 5 h / 20 °C

21.1: 97 percent / H₂ / Pd(OH)2 / ethanol / 1 h / 20 °C

22.1: 94 percent / pyridine / CH₂Cl₂ / 1 h / -78 - 0 °C

23.1: 66 percent / DMAP / CH₂Cl₂ / 6 h / 20 °C

24.1: 83 percent / tetrahydrofuran / 0.33 h / -78 °C

25.1: 88 percent / HF*pyridine / tetrahydrofuran / 2 h / 20 °C

26.1: 94 percent / pyridine / CH₂Cl₂ / 3 h / 20 °C

27.1: 80 percent / TASF / tetrahydrofuran / 48 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; methanol; dmap; N-chloro-succinimide; osmium(VIII) oxide; samarium diiodide; oxodiperoxymolybdenumpyridine hexamethylphosphoric triamide complex; 2-Methoxypropene; 2,6-dichloro-benzonitrile; tetrabutyl ammonium fluoride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; hydrogen; dihydrogen peroxide; 2,6-di-tert-butyl-4-hydroxytoluene; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium carbonate; potassium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; palladium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 1.1: cyclocondensation / 2.1: Ring cleavage / 3.1: Ring cleavage / 4.1: desilylation / 4.2: Isomerization / 5.1: cyclocondensation / 6.1: silylation / 7.1: Ring cleavage / 8.1: Dess-Martin oxidation / 9.1: Addition / 10.1: Metallation / 10.2: Condensation / 11.1: Condensation / 12.1: Chlorination / 13.1: Elimination / 14.1: hydroxylation / 15.1: Acetylation / 16.1: Isomerization / 17.1: hydroxylation / 18.1: Cyclization / 19.1: cleavage / 20.1: silylation / 21.1: Hydrogenolysis / 22.1: cyclocond;

DOI:10.1021/ja9939439

upstream raw materials:

10-deacetylbaccatin III

2,2,2-Trichloroethyl chloroformate

baccatin III

C₄₀H₅₃Cl₃O₁₃Si

Downstream raw materials:

baccatin III 13-(S-3-phenyllactate)

baccatin III 13-((R)-3-phenyllactate)

baccatin III 13-((R)-lactate)

baccatin III 13-((S)-lactate)

Refernces

• 1、 -. "Novel taxane anti-tumor compound as well as synthesis method and application thereof". Paragraph 0019. . Retrieved 2017/08/29.
• 2、 Morihira,Hara,Kawahara,Nishimori,Nakamura,Kusama,Kuwajima. "Enantioselective total synthesis of taxol [13]". . p. 12980 - 12981. Retrieved 2007/10/03.