Benzoic acid (1S,2S,3S,4S,7S,8S,10R,13S)-4-acetoxy-1,13-dihydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-5,11-dien-2-yl ester

Base Information

• Chemical Name: Benzoic acid (1S,2S,3S,4S,7S,8S,10R,13S)-4-acetoxy-1,13-dihydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-5,11-dien-2-yl ester
• CAS No.: 646502-79-6
• Molecular Formula: C₄₀H₆₂O₉Si₂
• Molecular Weight: 743.098
• Mol file: 646502-79-6.mol

Synonyms:Benzoic acid (1S,2S,3S,4S,7S,8S,10R,13S)-4-acetoxy-1,13-dihydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-5,11-dien-2-yl ester

Chemical Property of Benzoic acid (1S,2S,3S,4S,7S,8S,10R,13S)-4-acetoxy-1,13-dihydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-5,11-dien-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1S,2S,3S,4S,7S,8S,10R,13S)-4-acetoxy-1,13-dihydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-5,11-dien-2-yl ester

There total 7 articles about Benzoic acid (1S,2S,3S,4S,7S,8S,10R,13S)-4-acetoxy-1,13-dihydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-5,11-dien-2-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: 45.0%

Benzoic acid (1S,2S,3S,4S,7S,8S,10R)-4-acetoxy-1-hydroxy-8,12,15,15-tetramethyl-9,13-dioxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadeca-5,11-dien-2-yl ester (646502-78-5) → Benzoic acid (1S,2S,3S,4S,7S,8S,10R,13S)-4-acetoxy-1,13-dihydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadeca-5,11-dien-2-yl ester (646502-79-6) + Benzoic acid (1S,2S,3S,4S,7S,8S,10R,13R)-4-acetoxy-1,13-dihydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadeca-5,11-dien-2-yl ester

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 20 ℃;

DOI:10.1021/ol036043c

Reference yield:

phenyllithium (591-51-5) → Benzoic acid (1S,2S,3S,4S,7S,8S,10R,13S)-4-acetoxy-1,13-dihydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadeca-5,11-dien-2-yl ester (646502-79-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / tetrahydrofuran; cyclohexane / 0.33 h / -78 °C

2: 45 percent / NaBH₄ / methanol; tetrahydrofuran / 20 °C

With sodium tetrahydroborate; In tetrahydrofuran; methanol; cyclohexane;

DOI:10.1021/ol036043c

Reference yield:

2-debenzoyl-4-deacetyl-5α-bromo-7,10-di(triethylsilyl)-20-hydroxy-13-oxo-D-seco-10-deacetylbaccatin III 1,2 carbonate (285118-31-2) → Benzoic acid (1S,2S,3S,4S,7S,8S,10R,13S)-4-acetoxy-1,13-dihydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadeca-5,11-dien-2-yl ester (646502-79-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 98.8 percent / Pb(OAc)4 / acetonitrile / 1 h / 0 °C

2: 63.2 percent / (R)-2-methyl-CBS-oxazaborolidine; BH₃*Me₂S / tetrahydrofuran; toluene; CH₂Cl₂ / 0.17 h / -20 °C

3: 86 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / 40 °C

4: 48 percent / dimethylformamide / 1 h / 80 °C

5: 61 percent / tetrahydrofuran; cyclohexane / 0.33 h / -78 °C

6: 45 percent / NaBH₄ / methanol; tetrahydrofuran / 20 °C

With pyridine; lead(IV) acetate; dmap; sodium tetrahydroborate; dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ol036043c

upstream raw materials:

Benzoic acid (1S,2S,3S,4S,7S,8S,10R)-4-acetoxy-1-hydroxy-8,12,15,15-tetramethyl-9,13-dioxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-5,11-dien-2-yl ester

phenyllithium

2-debenzoyl-4-deacetyl-5α-bromo-7,10-di(triethylsilyl)-20-hydroxy-13-oxo-D-seco-10-deacetylbaccatin III 1,2 carbonate

C₃₄H₅₄O₉Si₂

Downstream raw materials:

2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-(4-acetoxy-2-benzoyloxy-1-hydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-5,11-dien-13-yl) ester 3-tert-butyl ester