Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1,4,5-trihydroxy-4-hydroxymethyl-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-tricyclo[9.3.1.0^3,8]pentadec-2-yl ester

Base Information

• Chemical Name: Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1,4,5-trihydroxy-4-hydroxymethyl-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-tricyclo[9.3.1.0^3,8]pentadec-2-yl ester
• CAS No.: 512781-00-9
• Molecular Formula: C₄₀H₅₆O₁₁Si
• Molecular Weight: 740.964

Synonyms:Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1,4,5-trihydroxy-4-hydroxymethyl-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-tricyclo[9.3.1.0^3,8]pentadec-2-yl ester

Chemical Property of Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1,4,5-trihydroxy-4-hydroxymethyl-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-tricyclo[9.3.1.0^3,8]pentadec-2-yl ester

Chemical Property:

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Technology Process of Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1,4,5-trihydroxy-4-hydroxymethyl-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-tricyclo[9.3.1.0^3,8]pentadec-2-yl ester

There total 5 articles about Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1,4,5-trihydroxy-4-hydroxymethyl-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-tricyclo[9.3.1.0^3,8]pentadec-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: 75.0%

Benzoic acid (1S,2S,3R,5S,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1,5-dihydroxy-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-4-methylene-9,14-dioxo-tricyclo[9.3.1.03,8]pentadec-2-yl ester (512780-97-1) → Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1,4,5-trihydroxy-4-hydroxymethyl-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-tricyclo[9.3.1.03,8]pentadec-2-yl ester (512781-00-9)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; osmium(VIII) oxide; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/jo0206566

Reference yield:

C40H54O9Si (512780-87-9) → Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1,4,5-trihydroxy-4-hydroxymethyl-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-tricyclo[9.3.1.03,8]pentadec-2-yl ester (512781-00-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 55 percent / 2,6-lutidine; triflic acid; DBU / toluene / 8 h / -78 - 0 °C

2: 55 percent / CSA / CH₂Cl₂ / 0.5 h / 20 °C

3: 90 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 48 h / 0 °C

4: 72 percent / Cp₂TiCl₂; zinc; ZnCl₂ / tetrahydrofuran / 0.17 h / 25 °C

5: 75 percent / osmium tetraoxide; DABCO / tetrahydrofuran / 24 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; bis(cyclopentadienyl)titanium dichloride; osmium(VIII) oxide; trifluorormethanesulfonic acid; camphor-10-sulfonic acid; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; zinc(II) chloride; zinc; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jo0206566

Reference yield:

Benzoic acid (1S,2S,3R,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-hydroxymethyl-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-tricyclo[9.3.1.03,8]pentadec-4-en-2-yl ester (512780-89-1) → Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1,4,5-trihydroxy-4-hydroxymethyl-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-tricyclo[9.3.1.03,8]pentadec-2-yl ester (512781-00-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 48 h / 0 °C

2: 72 percent / Cp₂TiCl₂; zinc; ZnCl₂ / tetrahydrofuran / 0.17 h / 25 °C

3: 75 percent / osmium tetraoxide; DABCO / tetrahydrofuran / 24 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; bis(cyclopentadienyl)titanium dichloride; osmium(VIII) oxide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; zinc(II) chloride; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo0206566

upstream raw materials:

Benzoic acid (1S,2S,3R,5S,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1,5-dihydroxy-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-4-methylene-9,14-dioxo-tricyclo[9.3.1.0^3,8]pentadec-2-yl ester

C₄₀H₅₄O₉Si

Benzoic acid (1S,2S,3R,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-hydroxymethyl-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-tricyclo[9.3.1.0^3,8]pentadec-4-en-2-yl ester

C₄₀H₅₄O₁₀Si

Downstream raw materials:

Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1,4-dihydroxy-4-hydroxymethyl-5-methanesulfonyloxy-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-tricyclo[9.3.1.0^3,8]pentadec-2-yl ester

Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1,4-dihydroxy-5-methanesulfonyloxy-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-4-trimethylsilanyloxymethyl-tricyclo[9.3.1.0^3,8]pentadec-2-yl ester

Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1,4,5-trihydroxy-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-4-trimethylsilanyloxymethyl-tricyclo[9.3.1.0^3,8]pentadec-2-yl ester

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