(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

Base Information

• Chemical Name: (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
• CAS No.: 266322-04-7
• Molecular Formula: C₂₅H₃₀N₂O₄SSi
• Molecular Weight: 482.676

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 5 articles about (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 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:

(E)-3-((R)-Toluene-4-sulfinyl)-prop-2-en-1-ol (92210-74-7) → (1R,5S,6R,7R,RS)-9-tert-butyldimethylsilyloxy-6-p-tolylsulfinyl-10-oxo-11-oxatricyclo[5.3.1.01,5]undec-8-ene-3,3-dicarbonitrile (266322-04-7)

Guidance literature:

Multi-step reaction with 3 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

3.1: toluene / 10 h / 110 °C

With sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

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

Reference yield:

(2E,RS)-methanesulfonic acid 3-(tolyl-4-sulfinyl)-allyl ester (266322-00-3) → (1R,5S,6R,7R,RS)-9-tert-butyldimethylsilyloxy-6-p-tolylsulfinyl-10-oxo-11-oxatricyclo[5.3.1.01,5]undec-8-ene-3,3-dicarbonitrile (266322-04-7)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 86 percent / tetrahydrofuran / 12 h / 20 °C

2.1: toluene / 10 h / 110 °C

With sodium hydride; In tetrahydrofuran; toluene;

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

Reference yield:

2-(bromomethyl)-3-((tert-butyldimethylsilyl)oxy)-4H-pyran-4-one (152547-42-7) → (1R,5S,6R,7R,RS)-9-tert-butyldimethylsilyloxy-6-p-tolylsulfinyl-10-oxo-11-oxatricyclo[5.3.1.01,5]undec-8-ene-3,3-dicarbonitrile (266322-04-7)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 75 percent / tetrahydrofuran / 1 h / -78 °C

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

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

3.1: toluene / 10 h / 110 °C

With sodium hydride; In tetrahydrofuran; toluene;

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

upstream raw materials:

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

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

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

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

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