(5Z,7E)-(1S,3R,24S)-9,10-seco-5,7,10(19)-cholestatriene-1,3,24,25-tetrol

Base Information

• Chemical Name: (5Z,7E)-(1S,3R,24S)-9,10-seco-5,7,10(19)-cholestatriene-1,3,24,25-tetrol
• CAS No.: 56142-95-1
• Molecular Formula: C₂₇H₄₄O₄
• Molecular Weight: 432.644
• DSSTox Substance ID: DTXSID801302097
• Wikidata: Q27132908
• Metabolomics Workbench ID: 35842
• ChEMBL ID: CHEMBL3542403
• Mol file: 56142-95-1.mol

Synonyms:CHEBI:63911;(5Z,7E)-(1S,3R,24S)-9,10-seco-5,7,10(19)-cholestatriene-1,3,24,25-tetrol;(24S)-1alpha,24,25-trihydroxyvitamin D3;(24S)-1alpha,24,25-trihydroxyvitamin D3 / (24S)-1alpha,24,25-trihydroxycholecalciferol;LMST03020294;CHEMBL3542403;DTXSID801302097;1alpha,24(S),25-Trihydroxyvitamin D3;(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,5S)-5,6-dihydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol;(24S)-1alpha,24,25-trihydroxycholecalciferol;Q27132908;(1S,3R,5Z,7E,24S)-9,10-secocholesta-5,7,10-triene-1,3,24,25-tetrol;56142-95-1

Chemical Property of (5Z,7E)-(1S,3R,24S)-9,10-seco-5,7,10(19)-cholestatriene-1,3,24,25-tetrol

Chemical Property:

• XLogP3: 3.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 432.32395988
• Heavy Atom Count: 31
• Complexity: 721

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CCC(C(C)(C)O)O)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C
• Isomeric SMILES: C[C@H](CC[C@@H](C(C)(C)O)O)[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 (5Z,7E)-(1S,3R,24S)-9,10-seco-5,7,10(19)-cholestatriene-1,3,24,25-tetrol

There total 14 articles about (5Z,7E)-(1S,3R,24S)-9,10-seco-5,7,10(19)-cholestatriene-1,3,24,25-tetrol 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(R),25-dihydroxycholecalciferol (55721-11-4,272776-87-1) → (1alpha,24R,25)-trihydroxy-Vitamin D3 (50648-94-7,56142-94-0,56142-95-1,65375-95-3,65375-96-4,72203-93-1,73837-27-1,78684-65-8)

Guidance literature:

With D-glucose 6-phosphate; bovine adrenodoxin reductase; mouse 25-hydroxyvitamin D3 1α-hydroxylase; mouse adrenodoxin; water; NADPH; glucose 6-phosphate dehydrogenase; at 37 ℃; pH=7.4; Concentration; Kinetics; aq. buffer; phospholipid vesicles; Enzymatic reaction;

DOI:10.1016/j.jsbmb.2010.02.022

Reference yield:

(1α,3β,5Z,7E,24R)-1,3-di[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(9)-triene-24,25-diol cyclic 24,25-(1-methylethylidene acetal) (474432-43-4) → (1alpha,24R,25)-trihydroxy-Vitamin D3 (50648-94-7,56142-94-0,56142-95-1,65375-95-3,65375-96-4,72203-93-1,73837-27-1,78684-65-8)

Guidance literature:

Multi-step reaction with 2 steps

1: nBu₄NF*3H₂O / tetrahydrofuran / 22 h

2: AG 50W-X₄ resin / methanol / 22 h

With AG 50W-X₄ resin; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol;

DOI:10.1002/1521-3765(20020617)8:12<2747::AID-CHEM2747>3.0.CO;2-J

Reference yield:

(1R,3aR,4S,7aR)-1-[(1R,4R)-4,5-dihydroxy-1,5-dimethylhexyl]-7a-methyl-octahydro-1H-inden-4-ol (226569-00-2) → (1alpha,24R,25)-trihydroxy-Vitamin D3 (50648-94-7,56142-94-0,56142-95-1,65375-95-3,65375-96-4,72203-93-1,73837-27-1,78684-65-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 89 percent / aq. H₂SO₄ / acetone / 2.5 h / ultrasonication

2.1: 99 percent / PDC / CH₂Cl₂ / 6 h

3.1: nBuLi / hexane; tetrahydrofuran / 5 h / -78 - 0 °C

3.2: 92 percent / tetrahydrofuran; hexane / 5 h / 20 °C

4.1: nBu₄NF*3H₂O / tetrahydrofuran / 22 h

5.1: AG 50W-X₄ resin / methanol / 22 h

With dipyridinium dichromate; n-butyllithium; AG 50W-X₄ resin; sulfuric acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone; 3.1: Wittig-Horner reaction / 3.2: Wittig-Horner reaction;

DOI:10.1002/1521-3765(20020617)8:12<2747::AID-CHEM2747>3.0.CO;2-J

upstream raw materials:

(1S,3R,9S,10R,13R,14R,17R)-17-((1R,4R)-4,5-Dihydroxy-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-1,3-diol

(1R,3aR,4S,7aR)-1-[(1R,4R)-4,5-dihydroxy-1,5-dimethylhexyl]-7a-methyl-octahydro-1H-inden-4-ol

(8β,24R)-de-A,B-cholesta-8,24,25-triol cyclic 24,25-(1-methylethylidene acetal)

(24R)-de-A,B-24,25-dihydroxycholestan-8-one cyclic 24,25-(1-methylethylidene acetal)