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

Base Information

• Chemical Name: diethyl 2-[(5-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]-2-[(R_S)-2-p-tolylsulfinyl-2-propenyl]malonate
• CAS No.: 439077-56-2
• Molecular Formula: C₂₉H₄₀O₈SSi
• Molecular Weight: 576.783

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

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

Chemical Property:

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

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

Methanesulfonic acid 2-((S)-toluene-4-sulfinyl)-allyl ester (439077-54-0) + diethyl 2-[(5-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]malonate (439079-38-6) → diethyl 2-[(5-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]-2-[(RS)-2-p-tolylsulfinyl-2-propenyl]malonate (439077-56-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

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

Reference yield:

(5-tert-butyldimethylsilyloxy-4-oxo-4H-pyran-2-yl)methyl chloride (152547-34-7) → diethyl 2-[(5-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]-2-[(RS)-2-p-tolylsulfinyl-2-propenyl]malonate (439077-56-2)

Guidance literature:

Multi-step reaction with 2 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

With sodium hydride; In tetrahydrofuran;

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

Reference yield:

diethyl malonate (105-53-3) → diethyl 2-[(5-tert-butyldimethylsilyloxy-4-oxo-4H-2-pyranyl)methyl]-2-[(RS)-2-p-tolylsulfinyl-2-propenyl]malonate (439077-56-2)

Guidance literature:

Multi-step reaction with 2 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

With sodium hydride; In tetrahydrofuran;

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

upstream raw materials:

Methanesulfonic acid 2-((S)-toluene-4-sulfinyl)-allyl ester

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

(5-tert-butyldimethylsilyloxy-4-oxo-4H-pyran-2-yl)methyl chloride

diethyl malonate

Downstream raw materials:

(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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