2,2-Dimethyl-propionic acid (1R,4R,9R,10R,13S)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-4-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (1R,4R,9R,10R,13S)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-4-yl ester
• CAS No.: 226910-64-1
• Molecular Formula: C₄₃H₆₂O₅Si
• Molecular Weight: 687.048

Synonyms:2,2-Dimethyl-propionic acid (1R,4R,9R,10R,13S)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-4-yl ester

Chemical Property of 2,2-Dimethyl-propionic acid (1R,4R,9R,10R,13S)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (1R,4R,9R,10R,13S)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-4-yl ester

There total 11 articles about 2,2-Dimethyl-propionic acid (1R,4R,9R,10R,13S)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-4-yl ester 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:

triethylsilyl trifluoromethyl sulfonate (79271-56-0) + 2,2-Dimethyl-propionic acid (1R,4R,9R,10R,13S)-9,10-bis-benzyloxy-13-hydroxy-12,15,15-trimethyl-tricyclo[9.3.1.03,8]pentadeca-3(8),11-dien-4-yl ester (226910-63-0) → 2,2-Dimethyl-propionic acid (1R,4R,9R,10R,13S)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadeca-3(8),11-dien-4-yl ester (226910-64-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -23 ℃; for 1h;

DOI:10.1021/ja984250f

Reference yield:

(R)-3-Benzyloxymethyl-5-[(S)-2-(bis-benzyloxy-methyl)-6-hydroxy-cyclohex-1-enylmethyl]-2,4,4-trimethyl-cyclohex-2-enone (226910-57-2) → 2,2-Dimethyl-propionic acid (1R,4R,9R,10R,13S)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadeca-3(8),11-dien-4-yl ester (226910-64-1)

Guidance literature:

Multi-step reaction with 8 steps

1: Ph₃P / tetrahydrofuran / 0.17 h / -23 °C

2: tetrahydrofuran / 168 h / Ambient temperature

3: t-BuOK / tetrahydrofuran / 1 h / 0 °C

4: tetrahydrofuran / 1 h / -78 °C

5: TMSOTf / CH₂Cl₂ / 1 h / -78 °C

6: 70 percent / TiCl₃(O-i-Pr) / CH₂Cl₂ / 1 h / -78 °C

7: lithium tri(t-butoxy)aluminum hydride / tetrahydrofuran / Ambient temperature

8: 2,6-lutidine / CH₂Cl₂ / 1 h / -23 °C

With 2,6-dimethylpyridine; titanium(IV) trichloride isopropoxide; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; lithium tri-t-butoxyaluminum hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja984250f

Reference yield:

(R)-3-Benzyloxymethyl-5-[(S)-2-(bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-2,4,4-trimethyl-cyclohex-2-enone (226910-56-1) → 2,2-Dimethyl-propionic acid (1R,4R,9R,10R,13S)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadeca-3(8),11-dien-4-yl ester (226910-64-1)

Guidance literature:

Multi-step reaction with 9 steps

1: TBAF / tetrahydrofuran / Ambient temperature

2: Ph₃P / tetrahydrofuran / 0.17 h / -23 °C

3: tetrahydrofuran / 168 h / Ambient temperature

4: t-BuOK / tetrahydrofuran / 1 h / 0 °C

5: tetrahydrofuran / 1 h / -78 °C

6: TMSOTf / CH₂Cl₂ / 1 h / -78 °C

7: 70 percent / TiCl₃(O-i-Pr) / CH₂Cl₂ / 1 h / -78 °C

8: lithium tri(t-butoxy)aluminum hydride / tetrahydrofuran / Ambient temperature

9: 2,6-lutidine / CH₂Cl₂ / 1 h / -23 °C

With 2,6-dimethylpyridine; titanium(IV) trichloride isopropoxide; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; tetrabutyl ammonium fluoride; lithium tri-t-butoxyaluminum hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja984250f

upstream raw materials:

triethylsilyl trifluoromethyl sulfonate

2,2-Dimethyl-propionic acid (1R,4R,9R,10R,13S)-9,10-bis-benzyloxy-13-hydroxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-4-yl ester

2,2-Dimethyl-propionic acid (1R,4R,9R,10R)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-oxo-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-4-yl ester

2,2-Dimethyl-propionic acid (1R,4R,9S,10R)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-oxo-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-4-yl ester

Downstream raw materials:

taxusin

C₃₃H₄₀O₄

C₃₉H₅₆O₄Si

C₃₉H₅₄O₄Si

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