(22E)-1-[(tert-butyldimethylsilyl)oxy]-2-methylene-24-oxo-25-hexanoyl-26,27-cyclo-22-dehydro-19-norvitamin D₃ tert-butyldimethylsilyl ether

Base Information

• Chemical Name: (22E)-1-[(tert-butyldimethylsilyl)oxy]-2-methylene-24-oxo-25-hexanoyl-26,27-cyclo-22-dehydro-19-norvitamin D₃ tert-butyldimethylsilyl ether
• CAS No.: 1417030-87-5
• Molecular Formula: C₄₅H₇₆O₄Si₂
• Molecular Weight: 737.267

Synonyms:(22E)-1-[(tert-butyldimethylsilyl)oxy]-2-methylene-24-oxo-25-hexanoyl-26,27-cyclo-22-dehydro-19-norvitamin D₃ tert-butyldimethylsilyl ether

Chemical Property of (22E)-1-[(tert-butyldimethylsilyl)oxy]-2-methylene-24-oxo-25-hexanoyl-26,27-cyclo-22-dehydro-19-norvitamin D₃ tert-butyldimethylsilyl ether

Chemical Property:

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Technology Process of (22E)-1-[(tert-butyldimethylsilyl)oxy]-2-methylene-24-oxo-25-hexanoyl-26,27-cyclo-22-dehydro-19-norvitamin D₃ tert-butyldimethylsilyl ether

There total 6 articles about (22E)-1-[(tert-butyldimethylsilyl)oxy]-2-methylene-24-oxo-25-hexanoyl-26,27-cyclo-22-dehydro-19-norvitamin D₃ tert-butyldimethylsilyl ether 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: 63.0%

1-[2-(dimethoxy-phosphoryl)-acetyl]-1-hexanoyl-cyclopropane (1203929-77-4) + (20S)-1-[(tert-butyldimethylsilyl)oxy]-2-methylene-22-oxo-19-nor-homopregnacalciferol tert-butyldimethylsilyl ether → (22E)-1-[(tert-butyldimethylsilyl)oxy]-2-methylene-24-oxo-25-hexanoyl-26,27-cyclo-22-dehydro-19-norvitamin D3 tert-butyldimethylsilyl ether (1417030-87-5)

Guidance literature:

1-[2-(dimethoxy-phosphoryl)-acetyl]-1-hexanoyl-cyclopropane; With lithium hexamethyldisilazane; In tetrahydrofuran; for 1h;

(20S)-1-[(tert-butyldimethylsilyl)oxy]-2-methylene-22-oxo-19-nor-homopregnacalciferol tert-butyldimethylsilyl ether; In tetrahydrofuran; for 72h;

Reference yield:

2,4-nonanedione (6175-23-1) → (22E)-1-[(tert-butyldimethylsilyl)oxy]-2-methylene-24-oxo-25-hexanoyl-26,27-cyclo-22-dehydro-19-norvitamin D3 tert-butyldimethylsilyl ether (1417030-87-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / acetone / 20 h / Reflux

2.1: triethylamine; triethylsilyl trifluoromethyl sulfonate / dichloromethane / 0.5 h / 0 °C

3.1: toluene / 20 h / Reflux

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h

4.2: 72 h

With triethylsilyl trifluoromethyl sulfonate; potassium carbonate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetone; toluene;

Reference yield:

n-pentyl methyl ketone (110-43-0) → (22E)-1-[(tert-butyldimethylsilyl)oxy]-2-methylene-24-oxo-25-hexanoyl-26,27-cyclo-22-dehydro-19-norvitamin D3 tert-butyldimethylsilyl ether (1417030-87-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / diethyl ether / 8 h / Reflux

2.1: potassium carbonate / acetone / 20 h / Reflux

3.1: triethylamine; triethylsilyl trifluoromethyl sulfonate / dichloromethane / 0.5 h / 0 °C

4.1: toluene / 20 h / Reflux

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h

5.2: 72 h

With triethylsilyl trifluoromethyl sulfonate; sodium hydride; potassium carbonate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene;

upstream raw materials:

2,4-nonanedione

n-pentyl methyl ketone

1-Acetyl-1-hexanoyl-cyclopropane

1-[2-(dimethoxy-phosphoryl)-acetyl]-1-hexanoyl-cyclopropane

Downstream raw materials:

(22E)-2-methylene-24-oxo-25-hexanoyl-26,27-cyclo-22-dehydro-hydroxy-19-norvitamin D₃

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