(1S,12R,16R)-17-Oxa-tricyclo[10.5.0.0^1,16]heptadec-13-ene-13,14-dicarboxylic acid 13-benzyl ester 14-methyl ester

Base Information

• Chemical Name: (1S,12R,16R)-17-Oxa-tricyclo[10.5.0.0^1,16]heptadec-13-ene-13,14-dicarboxylic acid 13-benzyl ester 14-methyl ester
• CAS No.: 162780-63-4
• Molecular Formula: C₂₆H₃₄O₅
• Molecular Weight: 426.553

Synonyms:(1S,12R,16R)-17-Oxa-tricyclo[10.5.0.0^1,16]heptadec-13-ene-13,14-dicarboxylic acid 13-benzyl ester 14-methyl ester

Chemical Property of (1S,12R,16R)-17-Oxa-tricyclo[10.5.0.0^1,16]heptadec-13-ene-13,14-dicarboxylic acid 13-benzyl ester 14-methyl ester

Chemical Property:

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Technology Process of (1S,12R,16R)-17-Oxa-tricyclo[10.5.0.0^1,16]heptadec-13-ene-13,14-dicarboxylic acid 13-benzyl ester 14-methyl ester

There total 4 articles about (1S,12R,16R)-17-Oxa-tricyclo[10.5.0.0^1,16]heptadec-13-ene-13,14-dicarboxylic acid 13-benzyl ester 14-methyl 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: 93.0%

(S)-3,5,6,7,8,9,10,11,12,13,14,14a-Dodecahydro-benzocyclododecene-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (162780-56-5) → (1S,12R,16R)-17-Oxa-tricyclo[10.5.0.01,16]heptadec-13-ene-13,14-dicarboxylic acid 13-benzyl ester 14-methyl ester (162780-63-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -20 ℃; for 48h;

DOI:10.1016/S0040-4039(00)78213-X

Reference yield:

(E)-1-vinylcyclododecene (94325-31-2) → (1S,12R,16R)-17-Oxa-tricyclo[10.5.0.01,16]heptadec-13-ene-13,14-dicarboxylic acid 13-benzyl ester 14-methyl ester (162780-63-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.0 M TiCl₄ / CH₂Cl₂ / 2 h / -78 °C

2: CH₂Cl₂ / 1 h / Ambient temperature

3: 93 percent / MCPBA / CH₂Cl₂ / 48 h / -20 °C

With titanium tetrachloride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/S0040-4039(00)78213-X

Reference yield:

(S)-1-Benzyl 4-methyl 2-p-tolylsulfinylmaleate (148871-72-1) → (1S,12R,16R)-17-Oxa-tricyclo[10.5.0.01,16]heptadec-13-ene-13,14-dicarboxylic acid 13-benzyl ester 14-methyl ester (162780-63-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.0 M TiCl₄ / CH₂Cl₂ / 2 h / -78 °C

2: CH₂Cl₂ / 1 h / Ambient temperature

3: 93 percent / MCPBA / CH₂Cl₂ / 48 h / -20 °C

With titanium tetrachloride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/S0040-4039(00)78213-X

upstream raw materials:

(S)-3,5,6,7,8,9,10,11,12,13,14,14a-Dodecahydro-benzocyclododecene-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

(E)-1-vinylcyclododecene

(S)-1-Benzyl 4-methyl 2-p-tolylsulfinylmaleate

(1R,2S,14aS)-1-((S)-Toluene-4-sulfinyl)-1,2,3,5,6,7,8,9,10,11,12,13,14,14a-tetradecahydro-benzocyclododecene-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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