(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-19,26,27-trinorvitamin D₃ tert-butyldimethylsilyl ether

Base Information

• Chemical Name: (20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-19,26,27-trinorvitamin D₃ tert-butyldimethylsilyl ether
• CAS No.: 1428964-47-9
• Molecular Formula: C₃₇H₆₈O₂Si₂
• Molecular Weight: 601.117

Synonyms:(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-19,26,27-trinorvitamin D₃ tert-butyldimethylsilyl ether

Chemical Property of (20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-19,26,27-trinorvitamin D₃ tert-butyldimethylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-19,26,27-trinorvitamin D₃ tert-butyldimethylsilyl ether

There total 8 articles about (20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-19,26,27-trinorvitamin 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:

(20R)-des-A,B-20-butylpregnan-8-one (1428964-40-2) + [2-[(3'R,5'R)-3',5'-bis[(tert-butyldimethylsilyl)oxy]-4'-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (213250-64-7) → (20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-19,26,27-trinorvitamin D3 tert-butyldimethylsilyl ether (1428964-47-9)

Guidance literature:

[2-[(3'R,5'R)-3',5'-bis[(tert-butyldimethylsilyl)oxy]-4'-methylenecyclohexylidene]ethyl]diphenylphosphine oxide; With phenyllithium; In tetrahydrofuran; diethyl ether; cyclohexane; at -20 ℃; for 0.5h; Inert atmosphere;

(20R)-des-A,B-20-butylpregnan-8-one; In tetrahydrofuran; diethyl ether; cyclohexane; at -78 - 4 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.bioorg.2013.01.001

Reference yield:

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol (64190-52-9) → (20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-19,26,27-trinorvitamin D3 tert-butyldimethylsilyl ether (1428964-47-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dmap; triethylamine / dichloromethane / 22 h / 0 - 20 °C

2.1: potassium iodide / acetone / 18 h / Reflux

3.1: pyridine; nickel(II) chloride hexahydrate; zinc / 2 h / 50 - 65 °C

3.2: 0 - 20 °C

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 - 20 °C

5.1: dmap; triethylamine / dichloromethane / 22 h / 0 - 20 °C

6.1: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / 0 - 20 °C

7.1: pyridinium p-toluenesulfonate; pyridinium dichromate / dichloromethane / 5 h / 20 °C

8.1: phenyllithium / tetrahydrofuran; cyclohexane; diethyl ether / 0.5 h / -20 °C / Inert atmosphere

8.2: 24 h / -78 - 4 °C / Inert atmosphere

With pyridine; dmap; lithium aluminium tetrahydride; pyridinium dichromate; nickel(II) chloride hexahydrate; pyridinium p-toluenesulfonate; phenyllithium; triethylamine; potassium iodide; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; acetone;

DOI:10.1016/j.bioorg.2013.01.001

Reference yield:

(8S,20R)-des-A,B-20-[(3'-iso-propoxycarbonyl)propyl]pregnan-8-ol (1428964-30-0) → (20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-19,26,27-trinorvitamin D3 tert-butyldimethylsilyl ether (1428964-47-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 - 20 °C

2.1: dmap; triethylamine / dichloromethane / 22 h / 0 - 20 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / 0 - 20 °C

4.1: pyridinium p-toluenesulfonate; pyridinium dichromate / dichloromethane / 5 h / 20 °C

5.1: phenyllithium / tetrahydrofuran; cyclohexane; diethyl ether / 0.5 h / -20 °C / Inert atmosphere

5.2: 24 h / -78 - 4 °C / Inert atmosphere

With dmap; lithium aluminium tetrahydride; pyridinium dichromate; pyridinium p-toluenesulfonate; phenyllithium; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane;

DOI:10.1016/j.bioorg.2013.01.001

upstream raw materials:

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol

(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol

(8S,20R)-des-A,B-20-[(3'-iso-propoxycarbonyl)propyl]pregnan-8-ol

(8S,20R)-des-A,B-20-(4'-hydroxybutyl)pregnan-8-ol

Downstream raw materials:

(20R)-2-methylene-19,26,27-trinor-1α,25-dihydroxyvitamin D₃

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