(1S,3R,7S,8S,9R,10R)-9-Benzyloxymethyl-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-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-(2-trimethylsilanyl-ethoxymethoxymethyl)-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.0^3,8]undecane-5,11-dione
• CAS No.: 814919-97-6
• Molecular Formula: C₂₈H₄₄O₇Si₂
• Molecular Weight: 548.824

Synonyms:(1S,3R,7S,8S,9R,10R)-9-Benzyloxymethyl-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-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-(2-trimethylsilanyl-ethoxymethoxymethyl)-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-(2-trimethylsilanyl-ethoxymethoxymethyl)-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.0^3,8]undecane-5,11-dione

There total 5 articles about (1S,3R,7S,8S,9R,10R)-9-Benzyloxymethyl-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-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: 83.0%

(1S,3R,7S,8S,9R,10S)-9-Benzyloxymethyl-11-methylene-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.03,8]undecan-5-one (814919-98-7) → (1S,3R,7S,8S,9R,10R)-9-Benzyloxymethyl-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.03,8]undecane-5,11-dione (814919-97-6)

Guidance literature:

(1S,3R,7S,8S,9R,10S)-9-Benzyloxymethyl-11-methylene-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.0^3,8]undecan-5-one; With ozone; In dichloromethane; at -78 ℃; for 0.25h;

With triphenylphosphine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/jo048681u

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-(2-trimethylsilanyl-ethoxymethoxymethyl)-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.03,8]undecane-5,11-dione (814919-97-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 29 percent / diacetoxyiodobenzene; iodine / CH₂Cl₂ / 0.83 h / 0 °C / Irradiation

2.1: 86 percent / i-Pr₂NEt / CH₂Cl₂ / 10 h / 20 °C

3.1: O₃ / CH₂Cl₂ / 0.25 h / -78 °C

3.2: 83 percent / PPh₃ / CH₂Cl₂ / -78 - 20 °C

With [bis(acetoxy)iodo]benzene; iodine; ozone; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo048681u

Reference yield:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → (1S,3R,7S,8S,9R,10R)-9-Benzyloxymethyl-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.03,8]undecane-5,11-dione (814919-97-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 86 percent / i-Pr₂NEt / CH₂Cl₂ / 10 h / 20 °C

2.1: O₃ / CH₂Cl₂ / 0.25 h / -78 °C

2.2: 83 percent / PPh₃ / CH₂Cl₂ / -78 - 20 °C

With ozone; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo048681u

upstream raw materials:

(1S,3R,7S,8S,9R,10S)-9-Benzyloxymethyl-11-methylene-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.0^3,8]undecan-5-one

(2-trimethylethylsilylethoxy)methyl chloride

(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

Downstream raw materials:

C₄₈H₇₇IO₈Si₂

C₄₈H₇₇IO₈Si₂

C₄₈H₇₅IO₈Si₂

C₄₈H₇₆O₈Si₂

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