4H-Pyran-4-one, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-[[[(2E)-3-[(R)-(4-methylphenyl) sulfinyl]-2-propenyl]thio]methyl]-

Base Information

• Chemical Name: 4H-Pyran-4-one, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-[[[(2E)-3-[(R)-(4-methylphenyl) sulfinyl]-2-propenyl]thio]methyl]-
• CAS No.: 266322-03-6
• Molecular Formula: C22H30O4S2Si
• Molecular Weight: 450.695
• Mol file: 266322-03-6.mol

Synonyms:

Chemical Property of 4H-Pyran-4-one, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-[[[(2E)-3-[(R)-(4-methylphenyl) sulfinyl]-2-propenyl]thio]methyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4H-Pyran-4-one, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-[[[(2E)-3-[(R)-(4-methylphenyl) sulfinyl]-2-propenyl]thio]methyl]-

There total 2 articles about 4H-Pyran-4-one, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-[[[(2E)-3-[(R)-(4-methylphenyl) sulfinyl]-2-propenyl]thio]methyl]- 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: 71.0%

2-(bromomethyl)-3-((tert-butyldimethylsilyl)oxy)-4H-pyran-4-one (152547-42-7) + (2E,RS)-methanesulfonic acid 3-(tolyl-4-sulfinyl)-allyl ester (266322-00-3) → 3-tert-butyldimethylsilyloxy-2-[((2E,RS)-3-p-tolylsulfinyl-2-propenyl)sulfanylmethyl]-4H-4-pyranone (266322-03-6)

Guidance literature:

(2E,R_S)-methanesulfonic acid 3-(tolyl-4-sulfinyl)-allyl ester; With caesium carbonate; triphenylphosphine; HSiPh₃; In tetrahydrofuran; at -5 ℃; for 0.25h;

2-(bromomethyl)-3-((tert-butyldimethylsilyl)oxy)-4H-pyran-4-one; In tetrahydrofuran; at 20 ℃; for 10h; Further stages.;

DOI:10.1002/1521-3765(20020215)8:4<884::AID-CHEM884>3.0.CO;2-Q

Reference yield:

(E)-3-((R)-Toluene-4-sulfinyl)-prop-2-en-1-ol (92210-74-7) → 3-tert-butyldimethylsilyloxy-2-[((2E,RS)-3-p-tolylsulfinyl-2-propenyl)sulfanylmethyl]-4H-4-pyranone (266322-03-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

2.1: Ph₃SiSH; PPh₃; Cs₂CO₃ / tetrahydrofuran / 0.25 h / -5 °C

2.2: 71 percent / tetrahydrofuran / 10 h / 20 °C

With caesium carbonate; triethylamine; triphenylphosphine; HSiPh₃; In tetrahydrofuran; dichloromethane;

DOI:10.1002/1521-3765(20020215)8:4<884::AID-CHEM884>3.0.CO;2-Q

Reference yield:

3-tert-butyldimethylsilyloxy-2-[((2E,RS)-3-p-tolylsulfinyl-2-propenyl)sulfanylmethyl]-4H-4-pyranone (266322-03-6) → (1S,5S,6S,7S,RS)-9-tert-butyldimethylsilyloxy-6-p-tolylsulfinyl-11-oxa-3-thiatricyclo[5.3.1.01,5]undec-8-ene-10-one + (1R,5R,6R,7R,RS)-9-tert-butyldimethylsilyloxy-6-p-tolylsulfinyl-11-oxa-3-thiatricyclo[5.3.1.01,5]undec-8-ene-10-one (266322-06-9)

Guidance literature:

In toluene; for 46h; Heating;

DOI:10.1021/ol005724u

upstream raw materials:

2-(bromomethyl)-3-((tert-butyldimethylsilyl)oxy)-4H-pyran-4-one

(2E,R_S)-methanesulfonic acid 3-(tolyl-4-sulfinyl)-allyl ester

(E)-3-((R)-Toluene-4-sulfinyl)-prop-2-en-1-ol

Downstream raw materials:

(1R,5R,6R,7R,R_S)-9-tert-butyldimethylsilyloxy-6-p-tolylsulfinyl-11-oxa-3-thiatricyclo[5.3.1.0^1,5]undec-8-ene-10-one