Benzoic acid (1S,2S,3S,4S,6R,9S)-6-acetoxy-3-((R)-2-benzyloxymethoxy-1-methylene-4-oxo-butyl)-1-hydroxy-4,8,11,11-tetramethyl-5-oxo-9-triisopropylsilanyloxy-bicyclo[5.3.1]undec-7-en-2-yl ester

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Chemical Name:Benzoic acid (1S,2S,3S,4S,6R,9S)-6-acetoxy-3-((R)-2-benzyloxymethoxy-1-methylene-4-oxo-butyl)-1-hydroxy-4,8,11,11-tetramethyl-5-oxo-9-triisopropylsilanyloxy-bicyclo[5.3.1]undec-7-en-2-yl ester
CAS No.:187960-92-5
Molecular Formula:C₄₆H₆₄O₁₀Si
Molecular Weight:805.094
Hs Code.:

Benzoic acid (1S,2S,3S,4S,6R,9S)-6-acetoxy-3-((R)-2-benzyloxymethoxy-1-methylene-4-oxo-butyl)-1-hydroxy-4,8,11,11-tetramethyl-5-oxo-9-triisopropylsilanyloxy-bicyclo[5.3.1]undec-7-en-2-yl ester

Synonyms:Benzoic acid (1S,2S,3S,4S,6R,9S)-6-acetoxy-3-((R)-2-benzyloxymethoxy-1-methylene-4-oxo-butyl)-1-hydroxy-4,8,11,11-tetramethyl-5-oxo-9-triisopropylsilanyloxy-bicyclo[5.3.1]undec-7-en-2-yl ester

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Chemical Property of Benzoic acid (1S,2S,3S,4S,6R,9S)-6-acetoxy-3-((R)-2-benzyloxymethoxy-1-methylene-4-oxo-butyl)-1-hydroxy-4,8,11,11-tetramethyl-5-oxo-9-triisopropylsilanyloxy-bicyclo[5.3.1]undec-7-en-2-yl ester

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Technology Process of Benzoic acid (1S,2S,3S,4S,6R,9S)-6-acetoxy-3-((R)-2-benzyloxymethoxy-1-methylene-4-oxo-butyl)-1-hydroxy-4,8,11,11-tetramethyl-5-oxo-9-triisopropylsilanyloxy-bicyclo[5.3.1]undec-7-en-2-yl ester

There total 14 articles about Benzoic acid (1S,2S,3S,4S,6R,9S)-6-acetoxy-3-((R)-2-benzyloxymethoxy-1-methylene-4-oxo-butyl)-1-hydroxy-4,8,11,11-tetramethyl-5-oxo-9-triisopropylsilanyloxy-bicyclo[5.3.1]undec-7-en-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: 86.0%

: 187960-91-4
Benzoic acid (1S,2S,3S,4S,6R,9S)-6-acetoxy-3-((R)-2-benzyloxymethoxy-1-methylene-pent-4-enyl)-1-hydroxy-4,8,11,11-tetramethyl-5-oxo-9-triisopropylsilanyloxy-bicyclo[5.3.1]undec-7-en-2-yl ester

: 187960-92-5
Benzoic acid (1S,2S,3S,4S,6R,9S)-6-acetoxy-3-((R)-2-benzyloxymethoxy-1-methylene-4-oxo-butyl)-1-hydroxy-4,8,11,11-tetramethyl-5-oxo-9-triisopropylsilanyloxy-bicyclo[5.3.1]undec-7-en-2-yl ester

Guidance literature:: Benzoic acid (1S,2S,3S,4S,6R,9S)-6-acetoxy-3-((R)-2-benzyloxymethoxy-1-methylene-pent-4-enyl)-1-hydroxy-4,8,11,11-tetramethyl-5-oxo-9-triisopropylsilanyloxy-bicyclo[5.3.1]undec-7-en-2-yl ester; With ozone; In dichloromethane; at -78 ℃;

With triethyl phosphite; In dichloromethane;
DOI:10.1021/ja963539z

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 187960-92-5
Benzoic acid (1S,2S,3S,4S,6R,9S)-6-acetoxy-3-((R)-2-benzyloxymethoxy-1-methylene-4-oxo-butyl)-1-hydroxy-4,8,11,11-tetramethyl-5-oxo-9-triisopropylsilanyloxy-bicyclo[5.3.1]undec-7-en-2-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: N,N-diisopropylethylamine / 55 °C

2.1: NH₄F / methanol / 20 °C

3.1: tetrahydrofuran / -78 °C

4.1: DMAP; pyridine / tetrahydrofuran

5.1: 80 percent / 1,5,7-triazabicyclo[4.4.0]dec-5-ene / CH₂Cl₂ / 1 h / 20 °C

6.1: O₃ / CH₂Cl₂ / -78 °C

6.2: 86 percent / P(OEt)3 / CH₂Cl₂

With pyridine; dmap; ammonium fluoride; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; ozone; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; 1.1: Etherification / 2.1: desilylation / 3.1: Phenylation / 4.1: Acetylation / 5.1: Isomerization / 6.1: ozonolysis / 6.2: Reduction;
DOI:10.1021/ja963539z

Reference yield:

: 591-51-5
phenyllithium

: 187960-92-5
Benzoic acid (1S,2S,3S,4S,6R,9S)-6-acetoxy-3-((R)-2-benzyloxymethoxy-1-methylene-4-oxo-butyl)-1-hydroxy-4,8,11,11-tetramethyl-5-oxo-9-triisopropylsilanyloxy-bicyclo[5.3.1]undec-7-en-2-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrahydrofuran / -78 °C

2.1: DMAP; pyridine / tetrahydrofuran

3.1: 80 percent / 1,5,7-triazabicyclo[4.4.0]dec-5-ene / CH₂Cl₂ / 1 h / 20 °C

4.1: O₃ / CH₂Cl₂ / -78 °C

4.2: 86 percent / P(OEt)3 / CH₂Cl₂

With pyridine; dmap; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; ozone; In tetrahydrofuran; dichloromethane; 1.1: Phenylation / 2.1: Acetylation / 3.1: Isomerization / 4.1: ozonolysis / 4.2: Reduction;
DOI:10.1021/ja963539z