9,10-Secocholesta-5,7,10(19)-triene-3beta,25-diol

Base Information

• Chemical Name: 9,10-Secocholesta-5,7,10(19)-triene-3beta,25-diol
• CAS No.: 1233749-00-2
• Molecular Formula: C₂₇H₄₄O₂
• Molecular Weight: 400.645
• European Community (EC) Number: 252-891-2,242-990-9
• UNII: SN331791VY
• Wikipedia: Calcifediol
• Wikidata: Q27289296
• ChEMBL ID: CHEMBL3250186
• Mol file: 1233749-00-2.mol

Synonyms:SN331791VY;5,6-trans-25-Hydroxy vitamin D3;25-Hydroxycholecalciferol, 5-trans-;25-Hydroxy-5,6-trans-cholecalciferol;UNII-SN331791VY;1233749-00-2;(1S,3E)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol;9,10-Secocholesta-5,7,10(19)-triene-3beta,25-diol;Dedrogyl;36149-00-5;9,10-Secocholesta-5,7,10(19)-triene-3,25-diol, (3beta,5E,7E)-;Diaverene;Calcifediol hydrate;Calderol (TN);Cholecalciferol 25-hydroxy-;DTXSID0022721;5 6-cis-25-Hydroxyvitamin D3;C27H44O2.H2O;C27-H44-O2.H2-O;NCGC00161326-04;(S,E)-3-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-methylheptan-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-ylidene)ethylidene)-4-methylenecyclohexanol;19356-17-3;U 32070E;(3S,5Z,7E)-9,10-seco-5,7,10(19)-cholestatriene-3,25-diol;(5E,7E)-9,10-Seco-5,7,10(19)-cholestatrien-3beta,25-diol;DTXCID602721;SCHEMBL7901515;CHEMBL3250186;SCHEMBL15263247;5-trans-25-hydroxycholecalciferol;9,10-Secocholesta-5,7,10(19)-triene-3,25-diol, monohydrate, (3.beta.,5Z,7E)-;1h-indeno-1-pentanol, 4-[(2z)-2-[(5s)-5-hidroxi-2-metilenciclohexilideno]etilideno]octahidro-?,?,?,7a-tetrametil-, (?r,1r,3as,4e,7ar)-;CS-M3650;Tox21_111987;NCGC00161326-08;NCGC00179206-01;CAS-19356-17-3;Q27289296;(3S,5E,7E)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol;9,10-SECOCHOLESTA-5,7,10(19)-TRIENE-3,25-DIOL, (3.BETA.,5E,7E)-

Chemical Property of 9,10-Secocholesta-5,7,10(19)-triene-3beta,25-diol

Chemical Property:

• XLogP3: 6.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 400.334130642
• Heavy Atom Count: 29
• Complexity: 655

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
• Isomeric SMILES: C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C\3/C[C@H](CCC3=C)O)C
• Recent ClinicalTrials: Calcifediol in the Treatment of COVID 19
• Recent EU Clinical Trials: Prevention and treatment with Calcifediol of Coronavirus COVID-19-induced acute respiratory syndrome (SARS)

Technology Process of 9,10-Secocholesta-5,7,10(19)-triene-3beta,25-diol

There total 22 articles about 9,10-Secocholesta-5,7,10(19)-triene-3beta,25-diol 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: 72.0%

25-hydroxy-5E-[6,19,19'-H3]vitamin D3-3β-tert-butyldimethylsilyl ether (140710-90-3) → 3β,25-dihydroxy-9,10-secocholesta-5(E),7(E),10(19)-triene (1233749-00-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 48h;

Reference yield:

ergocalciferol acetate (2579-08-0) → 3β,25-dihydroxy-9,10-secocholesta-5(E),7(E),10(19)-triene (1233749-00-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 54 percent / lead tetraacetate, acetic acid / CH₂Cl₂ / 0 °C

2: 1.) O₃, 2.) triphenylphosphine / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C, 30 min

3: 1.) phenyllithium / 1.) THF, 2.) benzene, THF, 3 min

4: 85 percent / aq. acetic acid / tetrahydrofuran / 15 h

5: H₂, NaHCO₃; / 5percent Pt/C / benzene; ethanol / 24 h

6: NaOH / benzene; methanol / 0.33 h / Ambient temperature

7: 1.) hydrazine, 2.) dianisyl telluroxide / 1.) ethanol, reflux, overnight, 2.) water, CH₂Cl₂, 1,2-dibromotetrachloroethane, 5 h

With lead(IV) acetate; sodium hydroxide; di-(p-methoxyphenyl)tellurium oxide; hydrogen; sodium hydrogencarbonate; ozone; acetic acid; phenyllithium; triphenylphosphine; hydrazine; platinum on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; benzene;

DOI:10.1021/jo00375a013

Reference yield:

6(S),19-(N,N'-phthalhydrazido)-3β-acetoxy-20(S)-formyl-9,10-secopregna-5(10),7(E)-diene (104973-29-7) → 3β,25-dihydroxy-9,10-secocholesta-5(E),7(E),10(19)-triene (1233749-00-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) phenyllithium / 1.) THF, 2.) benzene, THF, 3 min

2: 85 percent / aq. acetic acid / tetrahydrofuran / 15 h

3: H₂, NaHCO₃; / 5percent Pt/C / benzene; ethanol / 24 h

4: NaOH / benzene; methanol / 0.33 h / Ambient temperature

5: 1.) hydrazine, 2.) dianisyl telluroxide / 1.) ethanol, reflux, overnight, 2.) water, CH₂Cl₂, 1,2-dibromotetrachloroethane, 5 h

With sodium hydroxide; di-(p-methoxyphenyl)tellurium oxide; hydrogen; sodium hydrogencarbonate; acetic acid; phenyllithium; hydrazine; platinum on activated charcoal; In tetrahydrofuran; methanol; ethanol; benzene;

DOI:10.1021/jo00375a013

upstream raw materials:

(3-bromo-1,1-dimethylpropoxy)triethylsilane

3β-<(triethylsilyl)oxy>-20(S)-<<(p-tolylsulfonyl)oxy>-methyl>-9,10-secopregna-5(E),7(E),10(19)-triene

6(S),19-(N,N'-phthalhydrazido)-3,25-dihydroxy-9,10-secocholesta-5⁽¹⁰⁾,7(E)-diene

Calciferol

Downstream raw materials:

3,5-Dinitro-benzoic acid (S)-3-[2-[(1R,3aS,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-4-methylene-cyclohexyl ester

calcidiol