(1S)-1,23-dihydroxy-24,25,26,27-tetranorcalciol

Base Information

• Chemical Name: (1S)-1,23-dihydroxy-24,25,26,27-tetranorcalciol
• CAS No.: 97903-37-2
• Molecular Formula: C₂₃H₃₆O₃
• Molecular Weight: 360.537
• DSSTox Substance ID: DTXSID201100219
• Wikidata: Q27120810
• Metabolomics Workbench ID: 35571
• Mol file: 97903-37-2.mol

Synonyms:1,23-dihydroxy-24,25,26,27-tetranorvitamin D3;1,23-DTNV-D3

Chemical Property of (1S)-1,23-dihydroxy-24,25,26,27-tetranorcalciol

Chemical Property:

• Vapor Pressure: 1.64E-13mmHg at 25°C
• Boiling Point: 531.4°Cat760mmHg
• Flash Point: 234.6°C
• PSA: 60.69000
• Density: 1.1g/cm³
• LogP: 4.14590
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 360.26644501
• Heavy Atom Count: 26
• Complexity: 590

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCO)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C
• Isomeric SMILES: C[C@H](CCO)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C[C@@H](C3=C)O)O)C

Technology Process of (1S)-1,23-dihydroxy-24,25,26,27-tetranorcalciol

There total 13 articles about (1S)-1,23-dihydroxy-24,25,26,27-tetranorcalciol 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

Refernces

• 1、 Rhieu, Steve Y.,Annalora, Andrew J.,Gathungu, Rose M.,Vouros, Paul,Uskokovic, Milan R.,Schuster, Inge,Palmore, G. Tayhas R.,Reddy, G. Satyanarayana. "A new insight into the role of rat cytochrome P450 24A1 in metabolism of selective analogs of 1α,25-dihydroxyvitamin D3". experimental part. p. 33 - 43. Retrieved 2012/03/07.