24,25,26,27-tetranor-1,23-(OH)2D₃

Base Information

• Chemical Name: 24,25,26,27-tetranor-1,23-(OH)2D₃
• CAS No.: 114030-51-2
• Molecular Formula: C₂₃H₃₆O₃
• Molecular Weight: 360.537
• Mol file: 114030-51-2.mol

Synonyms:

Chemical Property of 24,25,26,27-tetranor-1,23-(OH)2D₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 24,25,26,27-tetranor-1,23-(OH)2D₃

There total 13 articles about 24,25,26,27-tetranor-1,23-(OH)2D₃ 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: 78.0%

methyl 1α,3β-dihydroxy-9,10-seco-24-norchola-5,7-10(19)-trien-23-oate (71203-48-0) → 24,25,26,27-tetranor-1,23-(OH)2D3 (97903-37-2,114030-51-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 2.25h;

DOI:10.1039/c4ra04322g

Reference yield:

(R)-3-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)butanal (93489-71-5) → 24,25,26,27-tetranor-1,23-(OH)2D3 (97903-37-2,114030-51-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 2-methyl-but-2-ene; sodium chlorite; sodium dihydrogen phosphate monohydrate / tert-butyl alcohol; water / 1.5 h / 20 °C

2.1: toluene; diethyl ether; methanol / 1 h / 20 °C

3.1: trifluoroacetic acid / dichloromethane / 1.5 h / 0 °C

4.1: pyridinium chlorochromate / dichloromethane

5.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C

5.2: 5 h / -78 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

7.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.25 h / 0 - 20 °C

With sodium chlorite; lithium aluminium tetrahydride; n-butyllithium; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 5.1: |Wittig-Horner Reaction / 5.2: |Wittig-Horner Reaction;

DOI:10.1039/c4ra04322g

Reference yield:

(R)-methyl 3-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)butanoate → 24,25,26,27-tetranor-1,23-(OH)2D3 (97903-37-2,114030-51-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trifluoroacetic acid / dichloromethane / 1.5 h / 0 °C

2.1: pyridinium chlorochromate / dichloromethane

3.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C

3.2: 5 h / -78 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.25 h / 0 - 20 °C

With lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; 3.1: |Wittig-Horner Reaction / 3.2: |Wittig-Horner Reaction;

DOI:10.1039/c4ra04322g

upstream raw materials:

1α-hydroxy-24-oxavitamin D₃

calcitriol

(R)-3-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)butanenitrile

(R)-3-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)butanal