2’-TES-7-TROC-taxol

Base Information

• Chemical Name: 2’-TES-7-TROC-taxol
• CAS No.: 219780-99-1
• Molecular Formula: C₅₆H₆₆Cl₃NO₁₆Si
• Molecular Weight: 1143.58
• Mol file: 219780-99-1.mol

Synonyms:2’-TES-7-TROC-taxol

Chemical Property of 2’-TES-7-TROC-taxol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2’-TES-7-TROC-taxol

There total 50 articles about 2’-TES-7-TROC-taxol 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: 77.0%

7-(2,2,2-trichloroethyloxycarbonyl)baccatin III (103150-33-0) + (3R,4S)-1-benzoyl-4-phenyl-3-(triethylsilyl)oxy-2-azetidinone (149249-91-2) → 2’-TES-7-TROC-taxol (219780-99-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃;

DOI:10.1021/ja9824932

Reference yield:

C26H40O7Si (219780-79-7) → 2’-TES-7-TROC-taxol (219780-99-1)

Guidance literature:

Multi-step reaction with 28 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

28.1: 77 percent / LHMDS / tetrahydrofuran / -78 - 0 °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 hexamethyldisilazane; 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

Reference yield:

C32H48O6Si (219780-81-1) → 2’-TES-7-TROC-taxol (219780-99-1)

Guidance literature:

Multi-step reaction with 25 steps

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

1.2: 45 percent / sodium methoxide / methanol; tetrahydrofuran / 60 h / 20 °C

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

3.1: 2,6-lutidine / CH₂Cl₂ / 12 h / -45 °C

4.1: 6.6 mg / aq. hydrogen peroxide; aq. Na₂CO₃ / ethyl acetate / 1 h / 20 °C

5.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

6.1: 97 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 0.08 h / 20 °C

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

7.2: 89 percent / tetrahydrofuran / 1 h / -78 °C

8.1: 91 percent / tetrakis(triphenylphosphine)palladium / diethyl ether; tetrahydrofuran / 1 h / 20 °C

9.1: 88 percent / N-chlorosuccinimide / methanol / 10 h / 20 °C

10.1: 89 percent / pyridinium p-toluenesulfonate; 2-methoxypropene / CH₂Cl₂ / 0.05 h / 20 °C

11.1: 80 percent / lithium diisopropyl amide; MoO₅*pyridine*HMPA / tetrahydrofuran / 0.92 h / -23 °C

12.1: 92 percent / DMAP / CH₂Cl₂ / 0.5 h / 20 °C

13.1: 68 percent / DBN / toluene / 10 h / Heating

14.1: 86 percent / OsO₄; pyridine / diethyl ether; tetrahydrofuran / 18 h / 20 °C

15.1: 86 percent / DBU / toluene / 4 h / Heating

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

17.1: 15 mg / DMAP; imidazole / dimethylformamide / 5 h / 20 °C

18.1: 97 percent / H₂ / Pd(OH)2 / ethanol / 1 h / 20 °C

19.1: 94 percent / pyridine / CH₂Cl₂ / 1 h / -78 - 0 °C

20.1: 66 percent / DMAP / CH₂Cl₂ / 6 h / 20 °C

21.1: 83 percent / tetrahydrofuran / 0.33 h / -78 °C

22.1: 88 percent / HF*pyridine / tetrahydrofuran / 2 h / 20 °C

23.1: 94 percent / pyridine / CH₂Cl₂ / 3 h / 20 °C

24.1: 80 percent / TASF / tetrahydrofuran / 48 h / 20 °C

25.1: 77 percent / LHMDS / tetrahydrofuran / -78 - 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; N-chloro-succinimide; osmium(VIII) oxide; 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; Dess-Martin periodane; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; lithium diisopropyl amide; palladium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 1.1: desilylation / 1.2: Isomerization / 2.1: cyclocondensation / 3.1: silylation / 4.1: Ring cleavage / 5.1: Dess-Martin oxidation / 6.1: Addition / 7.1: Metallation / 7.2: Condensation / 8.1: Condensation / 9.1: Chlorination / 10.1: Elimination / 11.1: hydroxylation / 12.1: Acetylation / 13.1: Isomerization / 14.1: hydroxylation / 15.1: Cyclization / 16.1: cleavage / 17.1: silylation / 18.1: Hydrogenolysis / 19.1: cyclocondensation / 20.1: Acetylation / 21.1: Arylation / 22.1: desilylation / 2;

DOI:10.1021/ja9939439

upstream raw materials:

7-(2,2,2-trichloroethyloxycarbonyl)baccatin III

(3R,4S)-1-benzoyl-4-phenyl-3-(triethylsilyl)oxy-2-azetidinone

C₄₆H₆₆O₈Si₂

C₂₆H₃₄O₆

Downstream raw materials:

(2aR,4S,4aS,6R,9S,11S,12S,12bS)-6,12b-bis(acetyloxy)-9-({(2R,3S)-3-(benzoylamino)-3-phenyl-2-[(triethylsilyl)oxy]propanoyl}oxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9, 10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

taxol

Refernces

• 1、 Morihira,Hara,Kawahara,Nishimori,Nakamura,Kusama,Kuwajima. "Enantioselective total synthesis of taxol [13]". . p. 12980 - 12981. Retrieved 2007/10/03.