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

Base Information

• Chemical Name: (20R)-2-methylene-19,26,27-trinor-1α,25-dihydroxyvitamin D₃
• CAS No.: 1428964-29-7
• Molecular Formula: C₂₅H₄₀O₂
• Molecular Weight: 372.591
• Mol file: 1428964-29-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (20R)-2-methylene-19,26,27-trinor-1α,25-dihydroxyvitamin D₃ 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: 79.0%

(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-19,26,27-trinorvitamin D3 tert-butyldimethylsilyl ether (1428964-47-9) → (20R)-2-methylene-19,26,27-trinor-1α,25-dihydroxyvitamin D3 (1428964-29-7)

Guidance literature:

With hydrogen fluoride; In water; acetonitrile; at 0 - 20 ℃; for 3h;

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)-2-methylene-19,26,27-trinor-1α,25-dihydroxyvitamin D3 (1428964-29-7)

Guidance literature:

Multi-step reaction with 6 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

6.1: hydrogen fluoride / acetonitrile; water / 3 h / 0 - 20 °C

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

DOI:10.1016/j.bioorg.2013.01.001

Reference yield:

(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol (116535-65-0) → (20R)-2-methylene-19,26,27-trinor-1α,25-dihydroxyvitamin D3 (1428964-29-7)

Guidance literature:

Multi-step reaction with 7 steps

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

1.2: 0 - 20 °C

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

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

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

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

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

6.2: 24 h / -78 - 4 °C / Inert atmosphere

7.1: hydrogen fluoride / acetonitrile; water / 3 h / 0 - 20 °C

With pyridine; dmap; lithium aluminium tetrahydride; pyridinium dichromate; nickel(II) chloride hexahydrate; hydrogen fluoride; pyridinium p-toluenesulfonate; phenyllithium; triethylamine; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; water; acetonitrile;

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