(1S,3R,7S,8S,9R,10R)-9-Benzyloxymethyl-10-methoxymethoxymethyl-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.0^3,8]undecane-5,11-dione

Base Information

• Chemical Name: (1S,3R,7S,8S,9R,10R)-9-Benzyloxymethyl-10-methoxymethoxymethyl-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.0^3,8]undecane-5,11-dione
• CAS No.: 312924-00-8
• Molecular Formula: C₂₄H₃₄O₇Si
• Molecular Weight: 462.615

Synonyms:(1S,3R,7S,8S,9R,10R)-9-Benzyloxymethyl-10-methoxymethoxymethyl-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.0^3,8]undecane-5,11-dione

Chemical Property of (1S,3R,7S,8S,9R,10R)-9-Benzyloxymethyl-10-methoxymethoxymethyl-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.0^3,8]undecane-5,11-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,7S,8S,9R,10R)-9-Benzyloxymethyl-10-methoxymethoxymethyl-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.0^3,8]undecane-5,11-dione

There total 4 articles about (1S,3R,7S,8S,9R,10R)-9-Benzyloxymethyl-10-methoxymethoxymethyl-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.0^3,8]undecane-5,11-dione 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: 89.0%

(1S,3R,7S,8S,9R,10S)-9-Benzyloxymethyl-10-methoxymethoxymethyl-11-methylene-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.03,8]undecan-5-one (312923-98-1) → (1S,3R,7S,8S,9R,10R)-9-Benzyloxymethyl-10-methoxymethoxymethyl-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.03,8]undecane-5,11-dione (312924-00-8)

Guidance literature:

(1S,3R,7S,8S,9R,10S)-9-Benzyloxymethyl-10-methoxymethoxymethyl-11-methylene-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.0^3,8]undecan-5-one; With ozone; In dichloromethane; at -78 ℃;

With triphenylphosphine; In dichloromethane; at -78 - 20 ℃; Further stages.;

DOI:10.1021/ol000290o

Reference yield:

(1S,3R,7R,8S,9R,10S,11S)-9-Benzyloxymethyl-10-hydroxymethyl-11-methyl-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.03,8]undecan-5-one (312923-90-3) → (1S,3R,7S,8S,9R,10R)-9-Benzyloxymethyl-10-methoxymethoxymethyl-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.03,8]undecane-5,11-dione (312924-00-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 33 percent / I₂; PhI(OAc)2 / CH₂Cl₂ / 0 °C / Photolysis

2.1: 85 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: 89 percent / Ph₃P / CH₂Cl₂ / -78 - 20 °C

With [bis(acetoxy)iodo]benzene; iodine; ozone; N-ethyl-N,N-diisopropylamine; In dichloromethane; 1.1: Dehydrogenation / 2.1: Alkylation / 3.1: ozonation / 3.2: Ring cleavage;

DOI:10.1021/ol000290o

Reference yield:

(1S,3R,7S,8S,9R,10S)-9-Benzyloxymethyl-10-hydroxymethyl-11-methylene-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.03,8]undecan-5-one (312923-92-5) → (1S,3R,7S,8S,9R,10R)-9-Benzyloxymethyl-10-methoxymethoxymethyl-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.03,8]undecane-5,11-dione (312924-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 89 percent / Ph₃P / CH₂Cl₂ / -78 - 20 °C

With ozone; N-ethyl-N,N-diisopropylamine; In dichloromethane; 1.1: Alkylation / 2.1: ozonation / 2.2: Ring cleavage;

DOI:10.1021/ol000290o

upstream raw materials:

(1S,3R,7S,8S,9R,10S)-9-Benzyloxymethyl-10-methoxymethoxymethyl-11-methylene-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.0^3,8]undecan-5-one

(1S,3R,7R,8S,9R,10S,11S)-9-Benzyloxymethyl-10-hydroxymethyl-11-methyl-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.0^3,8]undecan-5-one

(1S,3R,7S,8S,9R,10S)-9-Benzyloxymethyl-10-hydroxymethyl-11-methylene-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.0^3,8]undecan-5-one

C₂₀H₂₂O₅C₃H₉SiI

Downstream raw materials:

C₂₆H₃₃O₉C₆H₁₅Si

C₂₅H₃₅O₈C₆H₁₅Si

C₂₅H₃₃O₇BrC₄H₈O

C₂₆H₃₄O₉

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