(1R,5R,7R)-9-(tert-Butyl-dimethyl-silanyloxy)-8-oxo-5-((S)-toluene-4-sulfinyl)-11-oxa-tricyclo[5.3.1.0^1,5]undec-9-ene-3,3-dicarboxylic acid diethyl ester

Base Information

• Chemical Name: (1R,5R,7R)-9-(tert-Butyl-dimethyl-silanyloxy)-8-oxo-5-((S)-toluene-4-sulfinyl)-11-oxa-tricyclo[5.3.1.0^1,5]undec-9-ene-3,3-dicarboxylic acid diethyl ester
• CAS No.: 439077-62-0
• Molecular Formula: C₂₉H₄₀O₈SSi
• Molecular Weight: 576.783

Synonyms:(1R,5R,7R)-9-(tert-Butyl-dimethyl-silanyloxy)-8-oxo-5-((S)-toluene-4-sulfinyl)-11-oxa-tricyclo[5.3.1.0^1,5]undec-9-ene-3,3-dicarboxylic acid diethyl ester

Chemical Property of (1R,5R,7R)-9-(tert-Butyl-dimethyl-silanyloxy)-8-oxo-5-((S)-toluene-4-sulfinyl)-11-oxa-tricyclo[5.3.1.0^1,5]undec-9-ene-3,3-dicarboxylic acid diethyl ester

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Technology Process of (1R,5R,7R)-9-(tert-Butyl-dimethyl-silanyloxy)-8-oxo-5-((S)-toluene-4-sulfinyl)-11-oxa-tricyclo[5.3.1.0^1,5]undec-9-ene-3,3-dicarboxylic acid diethyl ester

There total 3 articles about (1R,5R,7R)-9-(tert-Butyl-dimethyl-silanyloxy)-8-oxo-5-((S)-toluene-4-sulfinyl)-11-oxa-tricyclo[5.3.1.0^1,5]undec-9-ene-3,3-dicarboxylic acid diethyl 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: 93.0%

diethyl 2-[(5-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]-2-[(RS)-2-p-tolylsulfinyl-2-propenyl]malonate (439077-56-2) → (1R,5R,7R)-9-(tert-Butyl-dimethyl-silanyloxy)-8-oxo-5-((S)-toluene-4-sulfinyl)-11-oxa-tricyclo[5.3.1.01,5]undec-9-ene-3,3-dicarboxylic acid diethyl ester (439077-62-0)

Guidance literature:

In toluene; at 110 ℃; for 4h;

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

Reference yield:

diethyl malonate (105-53-3) → (1R,5R,7R)-9-(tert-Butyl-dimethyl-silanyloxy)-8-oxo-5-((S)-toluene-4-sulfinyl)-11-oxa-tricyclo[5.3.1.01,5]undec-9-ene-3,3-dicarboxylic acid diethyl ester (439077-62-0)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 75 percent / NaI / tetrahydrofuran / 4 h / 20 °C

2.1: 136 mg / NaH / tetrahydrofuran / 0.5 h / 20 °C

3.1: 93 percent / toluene / 4 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:

diethyl 2-[(5-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]malonate (439079-38-6) → (1R,5R,7R)-9-(tert-Butyl-dimethyl-silanyloxy)-8-oxo-5-((S)-toluene-4-sulfinyl)-11-oxa-tricyclo[5.3.1.01,5]undec-9-ene-3,3-dicarboxylic acid diethyl ester (439077-62-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 136 mg / NaH / tetrahydrofuran / 0.5 h / 20 °C

2: 93 percent / toluene / 4 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:

diethyl 2-[(5-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]-2-[(R_S)-2-p-tolylsulfinyl-2-propenyl]malonate

diethyl malonate

diethyl 2-[(5-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]malonate

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