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

Base Information

• Chemical Name: 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
• CAS No.: 226910-62-9
• Molecular Formula: C₃₇H₄₆O₅
• Molecular Weight: 570.769

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 7 articles about 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 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: 20.0%

2,2-Dimethyl-propionic acid (R)-2-{(R)-5-[1-benzyloxy-meth-(Z)-ylidene]-4,6,6-trimethyl-3-triisopropylsilanyloxy-cyclohex-3-enylmethyl}-3-(bis-benzyloxy-methyl)-cyclohex-2-enyl ester (226910-59-4) → 2,2-Dimethyl-propionic acid (1R,4R,9R,10R)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-oxo-tricyclo[9.3.1.03,8]pentadeca-3(8),11-dien-4-yl ester (226910-60-7) + 2,2-Dimethyl-propionic acid (1R,4R,9S,10R)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-oxo-tricyclo[9.3.1.03,8]pentadeca-3(8),11-dien-4-yl ester (226910-62-9)

Guidance literature:

With dimethylaluminum triflate; trifluorormethanesulfonic acid; In dichloromethane; at -45 ℃; for 1.5h;

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,9S,10R)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-oxo-tricyclo[9.3.1.03,8]pentadeca-3(8),11-dien-4-yl ester (226910-62-9)

Guidance literature:

Multi-step reaction with 5 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: 20 percent / Me₂AlOTf, TfOH / CH₂Cl₂ / 1.5 h / -45 °C

With dimethylaluminum triflate; trifluorormethanesulfonic acid; potassium tert-butylate; triphenylphosphine; In tetrahydrofuran; dichloromethane;

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) → 2,2-Dimethyl-propionic acid (1R,4R,9S,10R)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-oxo-tricyclo[9.3.1.03,8]pentadeca-3(8),11-dien-4-yl ester (226910-62-9)

Guidance literature:

Multi-step reaction with 3 steps

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

2: tetrahydrofuran / 1 h / -78 °C

3: 20 percent / Me₂AlOTf, TfOH / CH₂Cl₂ / 1.5 h / -45 °C

With dimethylaluminum triflate; trifluorormethanesulfonic acid; potassium tert-butylate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja984250f

upstream raw materials:

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

(R)-3-Benzyloxymethyl-5-[(S)-2-(bis-benzyloxy-methyl)-6-hydroxy-cyclohex-1-enylmethyl]-2,4,4-trimethyl-cyclohex-2-enone

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

(R)-3-Benzyloxymethyl-5-[(S)-2-(bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-2,4,4-trimethyl-cyclohex-2-enone

Downstream raw materials:

taxusin

C₃₃H₄₀O₄

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

(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

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