(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

Base Information

• Chemical Name: (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
• CAS No.: 814919-98-7
• Molecular Formula: C₂₉H₄₆O₆Si₂
• Molecular Weight: 546.852

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 3 articles about (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 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%

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) + (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,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)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 10h;

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,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)

Guidance literature:

Multi-step reaction with 2 steps

1: 29 percent / diacetoxyiodobenzene; iodine / CH₂Cl₂ / 0.83 h / 0 °C / Irradiation

2: 86 percent / i-Pr₂NEt / CH₂Cl₂ / 10 h / 20 °C

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

DOI:10.1021/jo048681u

Reference yield:

C20H22O5C3H9SiI (312923-94-7) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / zinc; acetic acid / methanol / 1 h / 20 °C

2: 86 percent / i-Pr₂NEt / CH₂Cl₂ / 10 h / 20 °C

With acetic acid; N-ethyl-N,N-diisopropylamine; zinc; In methanol; dichloromethane;

DOI:10.1021/jo048681u

upstream raw materials:

(2-trimethylethylsilylethoxy)methyl chloride

(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

(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

C₂₀H₂₂O₅C₃H₉SiI

Downstream raw materials:

C₄₈H₇₇IO₈Si₂

C₄₈H₇₇IO₈Si₂

C₄₈H₇₅IO₈Si₂

C₄₈H₇₆O₈Si₂

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