Lexacalcitol

Base Information

• Chemical Name: Lexacalcitol
• CAS No.: 131875-08-6
• Molecular Formula: C29H48O4
• Molecular Weight: 460.69
• UNII: 9G3DCA3958
• DSSTox Substance ID: DTXSID10869807
• Wikidata: Q27080264
• NCI Thesaurus Code: C80885
• Pharos Ligand ID: 2YXXXXJX77G8
• Metabolomics Workbench ID: 35975
• ChEMBL ID: CHEMBL432600
• Mol file: 131875-08-6.mol

Synonyms:20-epi-22-oxa-24a-homo-26,27-dimethyl-1alpha,25-dihydroxyvitamin D3;KH 1060;KH-1060;KH1060

Chemical Property of Lexacalcitol

Chemical Property:

• Vapor Pressure: 6.49E-17mmHg at 25°C
• Refractive Index: 1.541
• Boiling Point: 600.3 °C at 760 mmHg
• PKA: 14.43±0.40(Predicted)
• Flash Point: 316.8 °C
• PSA: 69.92000
• Density: 1.07 g/cm³
• LogP: 5.86380
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 460.35526001
• Heavy Atom Count: 33
• Complexity: 734

Purity/Quality:

98% ^*data from raw suppliers

Lexacalcitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CC)(CCCOC(C)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C)O
• Isomeric SMILES: CCC(CC)(CCCO[C@H](C)[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)O

Technology Process of Lexacalcitol

There total 9 articles about Lexacalcitol 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: 30.0%

6-((R)-1-{(1S,3aS,7aS)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-ethoxy)-3-ethyl-hexan-3-ol → lexacalcitol (131875-08-6,154461-85-5)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; at 20 ℃;

DOI:10.1016/S0968-0896(00)00267-4

Reference yield:

4-ethyl-hexane-1,4-diol (1113-00-4) → lexacalcitol (131875-08-6,154461-85-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / pyridine / 1 h / 0 °C

2: 2,6-lutidine / 1 h / 0 °C

3: 92 percent / NaI / dimethylformamide / 6 h / 20 °C

4: 86 percent / KH; 18-crown-6 / tetrahydrofuran / 20 °C

5: 81 percent / TFA / CH₂Cl₂ / 0.75 h / 0 °C

6: 80 percent / 4 Angstroem molecular sieves; PDC / CH₂Cl₂ / 1 h / 20 °C

7: 33 percent / NaHMDS / tetrahydrofuran / -60 - 20 °C

8: (dba)3Pd₂*CHCl₃; Ph₃P; Et₃N / toluene / 6 h / Heating

9: 30 percent / CSA / methanol / 20 °C

With 2,6-dimethylpyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; dipyridinium dichromate; 18-crown-6 ether; 4 A molecular sieve; camphor-10-sulfonic acid; sodium hexamethyldisilazane; potassium hydride; triethylamine; triphenylphosphine; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: esterification / 2: silylation / 3: substitution / 4: etherification / 5: hydrolysis / 6: oxidation / 7: Wittig reaction / 8: cyclocondensation / 9: hydrolysis;

DOI:10.1016/S0968-0896(00)00267-4

Reference yield:

Toluene-4-sulfonic acid 4-ethyl-4-hydroxy-hexyl ester (125573-88-8) → lexacalcitol (131875-08-6,154461-85-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 2,6-lutidine / 1 h / 0 °C

2: 92 percent / NaI / dimethylformamide / 6 h / 20 °C

3: 86 percent / KH; 18-crown-6 / tetrahydrofuran / 20 °C

4: 81 percent / TFA / CH₂Cl₂ / 0.75 h / 0 °C

5: 80 percent / 4 Angstroem molecular sieves; PDC / CH₂Cl₂ / 1 h / 20 °C

6: 33 percent / NaHMDS / tetrahydrofuran / -60 - 20 °C

7: (dba)3Pd₂*CHCl₃; Ph₃P; Et₃N / toluene / 6 h / Heating

8: 30 percent / CSA / methanol / 20 °C

With 2,6-dimethylpyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; dipyridinium dichromate; 18-crown-6 ether; 4 A molecular sieve; camphor-10-sulfonic acid; sodium hexamethyldisilazane; potassium hydride; triethylamine; triphenylphosphine; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: silylation / 2: substitution / 3: etherification / 4: hydrolysis / 5: oxidation / 6: Wittig reaction / 7: cyclocondensation / 8: hydrolysis;

DOI:10.1016/S0968-0896(00)00267-4

upstream raw materials:

4-ethyl-hexane-1,4-diol

Toluene-4-sulfonic acid 4-ethyl-4-hydroxy-hexyl ester

(20R)-De-A,B-24,26,27-trihomo-22-oxacholestane-8β,25-diol

(20R)-De-A,B-24,26,27-trihomo-25-hydroxy-22-oxacholestane-8-one

Refernces