1,25-Dihydroxy-19-norvitamin D3

Base Information

• Chemical Name: 1,25-Dihydroxy-19-norvitamin D3
• CAS No.: 130447-37-9
• Molecular Formula: C26H44 O3
• Molecular Weight: 404.63
• UNII: K5ZM856PSA
• Nikkaji Number: J527.620I
• Metabolomics Workbench ID: 35625
• ChEMBL ID: CHEMBL119386
• Mol file: 130447-37-9.mol

Synonyms:1,25-dihydroxy-19-norvitamin D3;1,3-cis-25-Dihydroxy-19-norvitamin D3;19-nor-22(E);1alpha,25-(OH)2-19-nor-vitamin D3;20-epi-19-nor-1,25-(OH)2 D3

Chemical Property of 1,25-Dihydroxy-19-norvitamin D3

Chemical Property:

• Vapor Pressure: 1.74E-14mmHg at 25°C
• Boiling Point: 552°C at 760 mmHg
• PKA: 14.34±0.40(Predicted)
• Flash Point: 234.1°C
• PSA: 60.69000
• Density: 1.121g/cm³
• LogP: 5.53860
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 404.32904526
• Heavy Atom Count: 29
• Complexity: 607

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CC(C3)O)O)C
• Isomeric SMILES: C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C3C[C@H](C[C@@H](C3)O)O)C

Technology Process of 1,25-Dihydroxy-19-norvitamin D3

There total 16 articles about 1,25-Dihydroxy-19-norvitamin 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: 60.0%

(1R,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-1-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-7a-methyl-octahydro-indene (139356-40-4) → 1α,25-dihydroxy-19-nor-vitamin D3 (130447-37-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h;

DOI:10.1016/0040-4039(91)80559-O

Reference yield:

methyl (-)-quinate (191916-39-9) → 1α,25-dihydroxy-19-nor-vitamin D3 (130447-37-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 70 percent / TEA / dimethylformamide / 18 h / Ambient temperature

3: DIBAL-H / toluene / 1 h / -78 °C

4: 80 percent / N-chlorosuccinimide-dimethylsulfide complex / CH₂Cl₂ / -25 - 0 °C

5: 1.) nBuLi 2.) H₂O₂ / 1.) a) 0 deg C b) -78 deg C, 30 min 2.) CHCl₃

6: 1.) nBuLi / 1.) THF, -78 deg C 2.) THF, -78 deg C, 1 h

7: 60 percent / Bu₄NF / tetrahydrofuran / 1 h

With n-butyllithium; N-chlorosuccinimide-dimethylsulfide; TEA; tetrabutyl ammonium fluoride; dihydrogen peroxide; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0040-4039(91)80559-O

Reference yield:

D-(-)-quinic acid (77-95-2) → 1α,25-dihydroxy-19-nor-vitamin D3 (130447-37-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / p-TsOH / 24 h / Ambient temperature

2: 70 percent / TEA / dimethylformamide / 18 h / Ambient temperature

4: DIBAL-H / toluene / 1 h / -78 °C

5: 80 percent / N-chlorosuccinimide-dimethylsulfide complex / CH₂Cl₂ / -25 - 0 °C

6: 1.) nBuLi 2.) H₂O₂ / 1.) a) 0 deg C b) -78 deg C, 30 min 2.) CHCl₃

7: 1.) nBuLi / 1.) THF, -78 deg C 2.) THF, -78 deg C, 1 h

8: 60 percent / Bu₄NF / tetrahydrofuran / 1 h

With n-butyllithium; N-chlorosuccinimide-dimethylsulfide; TEA; tetrabutyl ammonium fluoride; dihydrogen peroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0040-4039(91)80559-O

upstream raw materials:

25-hydroxyvitamin D₃

1α-acetoxy-25-hydroxy-3,5-cyclovitamin D3

Acetic acid (1R,3S,5S)-2-hydroxy-1-{(R)-2-[(3aS,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-1-methoxy-ethyl}-bicyclo[3.1.0]hex-3-yl ester

10-oxo-1α,25-dihydroxycyclovitamin D3

Refernces

• 1、 Perlman, Kato L.,Swenson, Rolf E.,Paaren, Herbert E.,Schnoes, Heinrich K.,DeLuca, Hector F.. "Novel synthesis of 19-nor-vitamin D compounds". . p. 7663 - 7666. Retrieved 1991.