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

Base Information

• Chemical Name: 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
• CAS No.: 226910-63-0
• Molecular Formula: C₃₇H₄₈O₅
• Molecular Weight: 572.785

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

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Technology Process of 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

There total 10 articles about 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 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 (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,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)

Guidance literature:

Multi-step reaction with 5 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

With titanium(IV) trichloride isopropoxide; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; 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 → 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)

Guidance literature:

Multi-step reaction with 4 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

With titanium(IV) trichloride isopropoxide; trimethylsilyl trifluoromethanesulfonate; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; dichloromethane;

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-13-hydroxy-12,15,15-trimethyl-tricyclo[9.3.1.03,8]pentadeca-3(8),11-dien-4-yl ester (226910-63-0)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1021/ja984250f

upstream raw materials:

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

(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

Downstream 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

taxusin

C₃₃H₄₀O₄

(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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