(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-ol

Base Information

• Chemical Name: (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-ol
• CAS No.: 226910-65-2
• Molecular Formula: C₃₈H₅₄O₄Si
• Molecular Weight: 602.93

Synonyms:(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-ol

Chemical Property of (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-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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-ol

There total 13 articles about (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-ol 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:

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) → (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-ol (226910-65-2)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 1h; Yield given;

DOI:10.1021/ja984250f

Reference yield:

2,2-Dimethyl-propionic acid (R)-2-((R)-3-benzyloxymethyl-2,2,4-trimethyl-5-oxo-cyclohex-3-enylmethyl)-3-(bis-benzyloxy-methyl)-cyclohex-2-enyl ester (226910-58-3) → (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-ol (226910-65-2)

Guidance literature:

Multi-step reaction with 7 steps

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

2: tetrahydrofuran / 1 h / -78 °C

3: TMSOTf / CH₂Cl₂ / 1 h / -78 °C

4: 70 percent / TiCl₃(O-i-Pr) / CH₂Cl₂ / 1 h / -78 °C

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

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

7: DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

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

DOI:10.1021/ja984250f

Reference yield:

2,2-Dimethyl-propionic acid (R)-2-{(R)-5-[1-benzyloxy-meth-(Z)-ylidene]-3-hydroxy-4,6,6-trimethyl-cyclohex-3-enylmethyl}-3-(bis-benzyloxy-methyl)-cyclohex-2-enyl ester → (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-ol (226910-65-2)

Guidance literature:

Multi-step reaction with 6 steps

1: tetrahydrofuran / 1 h / -78 °C

2: TMSOTf / CH₂Cl₂ / 1 h / -78 °C

3: 70 percent / TiCl₃(O-i-Pr) / CH₂Cl₂ / 1 h / -78 °C

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

5: 2,6-lutidine / CH₂Cl₂ / 1 h / -23 °C

6: DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

With 2,6-dimethylpyridine; titanium(IV) trichloride isopropoxide; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/ja984250f

upstream raw materials:

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

triethylsilyl trifluoromethyl sulfonate

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

C₃₉H₅₄O₄Si

C₃₉H₅₆O₄Si

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