24,25-Dihydroxyvitamin D

Base Information

• Chemical Name: 24,25-Dihydroxyvitamin D
• CAS No.: 40013-87-4
• Molecular Formula: C27H44O3
• Molecular Weight: 416.645
• Metabolomics Workbench ID: 37246
• NCI Thesaurus Code: C126931
• Wikidata: Q27161510
• Wikipedia: 24,25-Dihydroxycholecalciferol
• Mol file: 40013-87-4.mol

Synonyms:24,25-dihydroxy-vitamin D;24,25-dihydroxyvitamin D

Chemical Property of 24,25-Dihydroxyvitamin D

Chemical Property:

• Boiling Point: 571.1±35.0 °C(Predicted)
• PKA: 14.67±0.29(Predicted)
• Density: 1.06
• XLogP3: 5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 416.32904526
• Heavy Atom Count: 30
• Complexity: 688

Purity/Quality:

98% ^*data from raw suppliers

24(R,S),25-DihydroxyvitaminD3 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(C(C)(C)O)O)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
• Isomeric SMILES: C[C@H](CCC(C(C)(C)O)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@@H](CCC3=C)O)C

Technology Process of 24,25-Dihydroxyvitamin D

There total 34 articles about 24,25-Dihydroxyvitamin D 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:

→ 24,25-Dihydroxyvitamin D3 (40013-87-4,272776-87-1)

Guidance literature:

Reference yield:

3β-hydroxy-5-cholenoic acid (5255-17-4) → (24S)-24,25-dihydroxyvitamin D3 (40013-87-4,55700-58-8,55721-11-4,79434-72-3,81968-67-4,142864-50-4,272776-87-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) toluene-p-sulphonic acid, 2.) lithium aluminium hydride / 1.) benzene, room temperature, 2 h, 2.) THF, room temperature, 1 h

2: 3.26 g / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

3: 1.4 g / tetrahydrofuran / 3 h / Ambient temperature

4: 115.4 mg / pyridinium dichromate / CH₂Cl₂; dimethylformamide / 2 h / Ambient temperature

5: 35.8 mg / lithium aluminium hydride, ethanol, (S)-(-)-2,2'-dihydroxy-1,1'-binaphthyl / tetrahydrofuran / -90 °C

6: 49.2 mg / t-butyl hydroperoxide, VO(acac)2 / benzene / Ambient temperature

7: 11 mg / lithium aluminium hydride / tetrahydrofuran / Heating

8: 2M-aq. hydrochloric acid / methanol / Ambient temperature

With hydrogenchloride; tert.-butylhydroperoxide; lithium aluminium tetrahydride; dipyridinium dichromate; bis(acetylacetonate)oxovanadium; ethanol; (S)-[1,1']-binaphthalenyl-2,2'-diol; toluene-4-sulfonic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

Reference yield:

3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-ol (66414-43-5) → (24S)-24,25-dihydroxyvitamin D3 (40013-87-4,55700-58-8,55721-11-4,79434-72-3,81968-67-4,142864-50-4,272776-87-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 3.26 g / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

2: 1.4 g / tetrahydrofuran / 3 h / Ambient temperature

3: 115.4 mg / pyridinium dichromate / CH₂Cl₂; dimethylformamide / 2 h / Ambient temperature

4: 35.8 mg / lithium aluminium hydride, ethanol, (S)-(-)-2,2'-dihydroxy-1,1'-binaphthyl / tetrahydrofuran / -90 °C

5: 49.2 mg / t-butyl hydroperoxide, VO(acac)2 / benzene / Ambient temperature

6: 11 mg / lithium aluminium hydride / tetrahydrofuran / Heating

7: 2M-aq. hydrochloric acid / methanol / Ambient temperature

With hydrogenchloride; tert.-butylhydroperoxide; lithium aluminium tetrahydride; dipyridinium dichromate; bis(acetylacetonate)oxovanadium; ethanol; (S)-[1,1']-binaphthalenyl-2,2'-diol; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

upstream raw materials:

24(S),25-Dihydroxycholesterol

3β-hydroxy-5-cholenoic acid

3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-ol

3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-al

Refernces

• 1、 -. "Syntheses of 24R,25- and 24S,25-dihydroxycholecalciferol". . . Retrieved 2008/06/13.