(E)-3-{2-[(1S,2R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-cyclohexyl]-propane-1-sulfinyl}-acrylic acid methyl ester

Base Information

• Chemical Name: (E)-3-{2-[(1S,2R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-cyclohexyl]-propane-1-sulfinyl}-acrylic acid methyl ester
• CAS No.: 286838-13-9
• Molecular Formula: C₂₀H₃₈O₄SSi
• Molecular Weight: 402.671
• Mol file: 286838-13-9.mol

Synonyms:(E)-3-{2-[(1S,2R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-cyclohexyl]-propane-1-sulfinyl}-acrylic acid methyl ester

Chemical Property of (E)-3-{2-[(1S,2R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-cyclohexyl]-propane-1-sulfinyl}-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-{2-[(1S,2R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-cyclohexyl]-propane-1-sulfinyl}-acrylic acid methyl ester

There total 5 articles about (E)-3-{2-[(1S,2R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-cyclohexyl]-propane-1-sulfinyl}-acrylic 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: 90.0%

3-{2-[(1S,2R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-cyclohexyl]-propane-1-sulfinyl}-propionic acid methyl ester (286838-12-8) → (E)-3-{2-[(1S,2R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-cyclohexyl]-propane-1-sulfinyl}-acrylic acid methyl ester (286838-13-9)

Guidance literature:

With propynoic acid methyl ester; In toluene; for 2h; Heating;

DOI:10.1016/S0040-4020(00)00247-7

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (E)-3-{2-[(1S,2R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-cyclohexyl]-propane-1-sulfinyl}-acrylic acid methyl ester (286838-13-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 7.91 g / 2,6-lutidine / CH₂Cl₂ / 1 h / -72 °C

2: 88 percent / AIBN / tetrahydrofuran / 8 h / Heating

3: 439 mg / m-CPBA / CH₂Cl₂ / 4 h / -60 °C

4: 90 percent / methyl propiolate / toluene / 2 h / Heating

With 2,6-dimethylpyridine; 2,2'-azobis(isobutyronitrile); propynoic acid methyl ester; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene; 1: silylation / 2: Addition / 3: Oxidation / 4: metathesis;

DOI:10.1016/S0040-4020(00)00247-7

Reference yield:

isopulegol (7786-67-6,18674-65-2,20549-46-6,21290-09-5,29141-10-4,50373-36-9,59905-53-2,59905-54-3,96612-21-4,104870-56-6,121468-66-4,122517-60-6,122517-61-7,144541-38-8,89-79-2) → (E)-3-{2-[(1S,2R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-cyclohexyl]-propane-1-sulfinyl}-acrylic acid methyl ester (286838-13-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 7.91 g / 2,6-lutidine / CH₂Cl₂ / 1 h / -72 °C

2: 88 percent / AIBN / tetrahydrofuran / 8 h / Heating

3: 439 mg / m-CPBA / CH₂Cl₂ / 4 h / -60 °C

4: 90 percent / methyl propiolate / toluene / 2 h / Heating

With 2,6-dimethylpyridine; 2,2'-azobis(isobutyronitrile); propynoic acid methyl ester; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene; 1: silylation / 2: Addition / 3: Oxidation / 4: metathesis;

DOI:10.1016/S0040-4020(00)00247-7

upstream raw materials:

3-{2-[(1S,2R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-cyclohexyl]-propane-1-sulfinyl}-propionic acid methyl ester

t-butyldimethylsiyl triflate

isopulegol

tert-butyldimethyl(((1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl)oxy)silane