Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,13S)-10-acetoxy-5-bromo-1,2,4-trihydroxy-8,12,15,15-tetramethyl-9-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-13-triisopropylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-4-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,13S)-10-acetoxy-5-bromo-1,2,4-trihydroxy-8,12,15,15-tetramethyl-9-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-13-triisopropylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-4-ylmethyl ester
• CAS No.: 187961-10-0
• Molecular Formula: C₄₁H₅₈BrCl₃O₁₂Si
• Molecular Weight: 957.253

Synonyms:Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,13S)-10-acetoxy-5-bromo-1,2,4-trihydroxy-8,12,15,15-tetramethyl-9-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-13-triisopropylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-4-ylmethyl ester

Chemical Property of Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,13S)-10-acetoxy-5-bromo-1,2,4-trihydroxy-8,12,15,15-tetramethyl-9-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-13-triisopropylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-4-ylmethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,13S)-10-acetoxy-5-bromo-1,2,4-trihydroxy-8,12,15,15-tetramethyl-9-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-13-triisopropylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-4-ylmethyl ester

There total 10 articles about Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,13S)-10-acetoxy-5-bromo-1,2,4-trihydroxy-8,12,15,15-tetramethyl-9-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-13-triisopropylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-4-ylmethyl 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:

Benzoic acid (1S,2S,3S,4S,5S,9S)-3-((R)-2-benzyloxymethoxy-1-methylene-pent-4-enyl)-1,5-dihydroxy-4,8,11,11-tetramethyl-6-oxo-9-triisopropylsilanyloxy-bicyclo[5.3.1]undec-7-en-2-yl ester → Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,13S)-10-acetoxy-5-bromo-1,2,4-trihydroxy-8,12,15,15-tetramethyl-9-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-13-triisopropylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-4-ylmethyl ester (187961-10-0)

Guidance literature:

With 1H-imidazole; In chloroform;

DOI:10.1021/ja963539z

Reference yield:

C29H48O7Si (187960-83-4) → Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,13S)-10-acetoxy-5-bromo-1,2,4-trihydroxy-8,12,15,15-tetramethyl-9-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-13-triisopropylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-4-ylmethyl ester (187961-10-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 91 percent / tetrahydrofuran / -78 °C

2: 94 percent / HCl; H₂O; NaI / dioxane

3: 92 percent / pyridine / CH₂Cl₂ / -30 °C

4: Dess-Martin periodinane / CH₂Cl₂

5: Et₃N

6: 89 percent / ZnCl₂ / tetrahydrofuran / -78 °C

7: N,N-diisopropylethylamine / 55 °C

8: NH₄F / methanol / 20 °C

9: tetrahydrofuran / -78 °C

10: imidazole / CHCl₃

With pyridine; 1H-imidazole; hydrogenchloride; ammonium fluoride; water; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; zinc(II) chloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; 1: Wittig reaction / 2: Hydrolysis / 3: silylation / 4: Oxidation / 5: methylenation / 6: Grignard reaction / 7: Etherification / 8: desilylation / 9: Phenylation / 10: Isomerization;

DOI:10.1021/ja963539z

Reference yield:

((1S,5S,6R,7S,8S,9S,12S)-8,9-Dihydroxy-7,11,14,14-tetramethyl-3-oxo-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-en-6-yl)-acetaldehyde (187960-85-6) → Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,13S)-10-acetoxy-5-bromo-1,2,4-trihydroxy-8,12,15,15-tetramethyl-9-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-13-triisopropylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-4-ylmethyl ester (187961-10-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / pyridine / CH₂Cl₂ / -30 °C

2: Dess-Martin periodinane / CH₂Cl₂

3: Et₃N

4: 89 percent / ZnCl₂ / tetrahydrofuran / -78 °C

5: N,N-diisopropylethylamine / 55 °C

6: NH₄F / methanol / 20 °C

7: tetrahydrofuran / -78 °C

8: imidazole / CHCl₃

With pyridine; 1H-imidazole; ammonium fluoride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; chloroform; 1: silylation / 2: Oxidation / 3: methylenation / 4: Grignard reaction / 5: Etherification / 6: desilylation / 7: Phenylation / 8: Isomerization;

DOI:10.1021/ja963539z

upstream raw materials:

C₂₉H₄₈O₇Si

((1S,5S,6R,7S,8S,9S,12S)-8,9-Dihydroxy-7,11,14,14-tetramethyl-3-oxo-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.0^1,5]tetradec-10-en-6-yl)-acetaldehyde

((1S,5S,6R,7S,8S,9S,12S)-9-Hydroxy-7,11,14,14-tetramethyl-3-oxo-8-triethylsilanyloxy-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.0^1,5]tetradec-10-en-6-yl)-acetaldehyde

2-((1S,5S,6S,7S,8S,12S)-7,11,14,14-Tetramethyl-3,9-dioxo-8-triethylsilanyloxy-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.0^1,5]tetradec-10-en-6-yl)-propenal

Downstream raw materials:

C₄₂H₅₆BrCl₃O₁₃Si

10-deacetylbaccatin III

baccatin III

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