(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

Base Information

• Chemical Name: (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
• CAS No.: 312923-92-5
• Molecular Formula: C₂₃H₃₂O₅Si
• Molecular Weight: 416.59

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 3 articles about (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 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: 100.0%

C20H22O5C3H9SiI (312923-94-7) → (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)

Guidance literature:

With acetic acid; zinc; In methanol; at 20 ℃; for 1h;

DOI:10.1021/jo048681u

Reference yield: 33.0%

(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) → C20H23O5C3H9Si + (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) + C20H22O5C3H9SiI (312923-94-7)

Guidance literature:

With [bis(acetoxy)iodo]benzene; iodine; In dichloromethane; at 0 ℃; Photolysis;

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,10S)-9-Benzyloxymethyl-10-hydroxymethyl-11-methylene-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.03,8]undecan-5-one (312923-92-5)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 100 percent / zinc; acetic acid / methanol / 1 h / 20 °C

With [bis(acetoxy)iodo]benzene; iodine; acetic acid; zinc; In methanol; dichloromethane;

DOI:10.1021/jo048681u

upstream raw materials:

(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:

(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,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

C₂₇H₃₆O₇

C₂₈H₃₈O₆

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