[(1R,2R,4S,5S,6S)-6-(3-Methoxy-benzyl)-3-oxa-tricyclo[3.2.1.0^2,4]oct-6-yl]-propynoic acid methyl ester

Base Information

• Chemical Name: [(1R,2R,4S,5S,6S)-6-(3-Methoxy-benzyl)-3-oxa-tricyclo[3.2.1.0^2,4]oct-6-yl]-propynoic acid methyl ester
• CAS No.: 102939-71-9
• Molecular Formula: C₁₉H₂₀O₄
• Molecular Weight: 312.365

Synonyms:[(1R,2R,4S,5S,6S)-6-(3-Methoxy-benzyl)-3-oxa-tricyclo[3.2.1.0^2,4]oct-6-yl]-propynoic acid methyl ester

Chemical Property of [(1R,2R,4S,5S,6S)-6-(3-Methoxy-benzyl)-3-oxa-tricyclo[3.2.1.0^2,4]oct-6-yl]-propynoic acid methyl ester

Chemical Property:

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Technology Process of [(1R,2R,4S,5S,6S)-6-(3-Methoxy-benzyl)-3-oxa-tricyclo[3.2.1.0^2,4]oct-6-yl]-propynoic acid methyl ester

There total 5 articles about [(1R,2R,4S,5S,6S)-6-(3-Methoxy-benzyl)-3-oxa-tricyclo[3.2.1.0^2,4]oct-6-yl]-propynoic acid 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: 59.0%

[(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-en-2-yl]-propynoic acid methyl ester (102939-73-1) → [(1R,2R,4S,5S,6S)-6-(3-Methoxy-benzyl)-3-oxa-tricyclo[3.2.1.02,4]oct-6-yl]-propynoic acid methyl ester (102939-71-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 18h; from 0 deg C to room temperature;

DOI:10.1016/S0040-4039(00)98658-1

Reference yield:

(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde (102939-69-5) → [(1R,2R,4S,5S,6S)-6-(3-Methoxy-benzyl)-3-oxa-tricyclo[3.2.1.02,4]oct-6-yl]-propynoic acid methyl ester (102939-71-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent / Ph₃P / CH₂Cl₂ / 0 °C

2: 70 percent / n-buthyl-lithyum / tetrahydrofuran / -78 °C

3: 59 percent / m-CPBA / CH₂Cl₂ / 18 h / from 0 deg C to room temperature

With n-butyllithium; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)98658-1

Reference yield:

(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-ene-2-carbonitrile (102939-68-4) → [(1R,2R,4S,5S,6S)-6-(3-Methoxy-benzyl)-3-oxa-tricyclo[3.2.1.02,4]oct-6-yl]-propynoic acid methyl ester (102939-71-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / DIBAL-H / hexane; diethyl ether / 0 °C

2: 50 percent / Ph₃P / CH₂Cl₂ / 0 °C

3: 70 percent / n-buthyl-lithyum / tetrahydrofuran / -78 °C

4: 59 percent / m-CPBA / CH₂Cl₂ / 18 h / from 0 deg C to room temperature

With n-butyllithium; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1016/S0040-4039(00)98658-1

upstream raw materials:

[(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-en-2-yl]-propynoic acid methyl ester

(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde

(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-ene-2-carbonitrile

(1S,4S,5R)-5-(2,2-Dibromo-vinyl)-5-(3-methoxy-benzyl)-bicyclo[2.2.1]hept-2-ene

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