2-[(3-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]-2-[(2E,R_S)-3-p-tolylsulfinyl-2-propenyl]malononitrile

Base Information

• Chemical Name: 2-[(3-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]-2-[(2E,R_S)-3-p-tolylsulfinyl-2-propenyl]malononitrile
• CAS No.: 266322-01-4
• Molecular Formula: C₂₅H₃₀N₂O₄SSi
• Molecular Weight: 482.676

Synonyms:2-[(3-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]-2-[(2E,R_S)-3-p-tolylsulfinyl-2-propenyl]malononitrile

Chemical Property of 2-[(3-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]-2-[(2E,R_S)-3-p-tolylsulfinyl-2-propenyl]malononitrile

Chemical Property:

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Technology Process of 2-[(3-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]-2-[(2E,R_S)-3-p-tolylsulfinyl-2-propenyl]malononitrile

There total 2 articles about 2-[(3-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]-2-[(2E,R_S)-3-p-tolylsulfinyl-2-propenyl]malononitrile 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: 86.0%

(2E,RS)-methanesulfonic acid 3-(tolyl-4-sulfinyl)-allyl ester (266322-00-3) + 2-[3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-4H-pyran-2-ylmethyl]-malononitrile (439077-27-7) → 2-[(3-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]-2-[(2E,RS)-3-p-tolylsulfinyl-2-propenyl]malononitrile (266322-01-4)

Guidance literature:

2-[3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-4H-pyran-2-ylmethyl]-malononitrile; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.25h;

(2E,R_S)-methanesulfonic acid 3-(tolyl-4-sulfinyl)-allyl ester; In tetrahydrofuran; at 20 ℃; for 12h; 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) → 2-[(3-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]-2-[(2E,RS)-3-p-tolylsulfinyl-2-propenyl]malononitrile (266322-01-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2.1: NaH / tetrahydrofuran / 0.25 h / 20 °C

2.2: 86 percent / tetrahydrofuran / 12 h / 20 °C

With sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

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

Reference yield:

2-[(3-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]-2-[(2E,RS)-3-p-tolylsulfinyl-2-propenyl]malononitrile (266322-01-4) → 9-(tert-butyl-dimethyl-silanyloxy)-10-oxo-6-p-tolylsulfanyl-11-oxa-tricyclo[5.3.1.01,5]undec-8-ene-3,3-dicarbonitrile

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 10 h / 110 °C

2: 90 percent / PBr₃ / dimethylformamide / cooling

With phosphorus tribromide; In N,N-dimethyl-formamide; toluene;

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

upstream raw materials:

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

2-[3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-4H-pyran-2-ylmethyl]-malononitrile

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

Downstream raw materials:

(1R,5S,6R,7R,R_S)-9-tert-butyldimethylsilyloxy-6-p-tolylsulfinyl-10-oxo-11-oxatricyclo[5.3.1.0^1,5]undec-8-ene-3,3-dicarbonitrile

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