(5Z,7E,22E)-(1S,3R,24R)-9,10-seco-5,7,10(19),22-cholestatetraene-1,3,24-triol

Base Information

Chemical Name:(5Z,7E,22E)-(1S,3R,24R)-9,10-seco-5,7,10(19),22-cholestatetraene-1,3,24-triol
CAS No.:95270-41-0
Molecular Formula:C₂₇H₄₂O₃
Molecular Weight:414.629
Hs Code.:
Metabolomics Workbench ID:35718
Mol file:95270-41-0.mol

Synonyms:1,24-dihydroxy-22-dehydrocholecalciferol;1,24-dihydroxy-22-dehydrovitamin D3;1,24-dihydroxy-22-dehydrovitamin D3, (1alpha,3beta,5Z,7E,22E,24S)-isomer;1,24-OH-22-DH-D3

Suppliers and Price of (5Z,7E,22E)-(1S,3R,24R)-9,10-seco-5,7,10(19),22-cholestatetraene-1,3,24-triol

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (5Z,7E,22E)-(1S,3R,24R)-9,10-seco-5,7,10(19),22-cholestatetraene-1,3,24-triol

Chemical Property:

Vapor Pressure:2.74E-15mmHg at 25°C
Boiling Point:568.4°C at 760 mmHg
Flash Point:241.2°C
PSA：60.69000
Density:1.07g/cm³
LogP:5.33660
XLogP3:4.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:414.31339520
Heavy Atom Count:30
Complexity:716

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(C)C(C=CC(C)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C)O
Isomeric SMILES:C[C@H](/C=C/[C@@H](C(C)C)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,22E)-(1S,3R,24R)-9,10-seco-5,7,10(19),22-cholestatetraene-1,3,24-triol

There total 12 articles about (5Z,7E,22E)-(1S,3R,24R)-9,10-seco-5,7,10(19),22-cholestatetraene-1,3,24-triol 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:

: 1474-14-2
3β-acetoxybisnor-5-cholenic acid

: 95270-41-0
(22E,24R)-1α,24-dihydroxy-22-dehydrovitamin D₃

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) lithium aluminium hydride, 2.) dichlorodicyanobenzoquinone / 1.) THF, 60 degC, 14 h, 2.) dioxane, reflux, 14 h

2: 1.) p-toluenesulfonic acid, 2.) 30percent H₂O₂, 10percent NaOH / 1.) CH₂Cl₂, r.t. 1 h, 2.) MeOH, r.t. 14 h

3: Li, NH₄Cl / liquid ammonia; tetrahydrofuran / 4 h / -78 °C

4: pyridine / 14 h / Ambient temperature

5: 2 M HCl / methanol; tetrahydrofuran / 2 h / Ambient temperature

6: 82 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 1 h / Ambient temperature

7: 81 percent / dimethylsulfoxide / 72 h / 95 °C

8: 1.) N-bromosuccinimide, 2.) tetra-n-butylammonium bromide, tetra-n-butylammonium fluoride / 1.) carbon tetrachloride, reflux, 25 min., 2.) THF, r.t., 80 min.

9: 37 percent / CHCl₃ / 1 h / Ambient temperature

10: 43.1 percent / sodium borohydride / tetrahydrofuran; methanol / 0.17 h / Ambient temperature

11: 36 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / Heating

12: 1.) benzene, ethanol, irradiation, 2.5 min., 0 degC, 2.) reflux, 1 h

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; dihydrogen peroxide; sodium acetate; lithium; ammonium chloride; toluene-4-sulfonic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; ammonia; dimethyl sulfoxide;
DOI:10.1248/cpb.32.3866

Reference yield:

: 66875-12-5
(20S)-21-Hydroxy-20-methyl-1,4,6-pregnatrien-3-on

: 95270-41-0
(22E,24R)-1α,24-dihydroxy-22-dehydrovitamin D₃

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) p-toluenesulfonic acid, 2.) 30percent H₂O₂, 10percent NaOH / 1.) CH₂Cl₂, r.t. 1 h, 2.) MeOH, r.t. 14 h

2: Li, NH₄Cl / liquid ammonia; tetrahydrofuran / 4 h / -78 °C

3: pyridine / 14 h / Ambient temperature

4: 2 M HCl / methanol; tetrahydrofuran / 2 h / Ambient temperature

5: 82 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 1 h / Ambient temperature

6: 81 percent / dimethylsulfoxide / 72 h / 95 °C

7: 1.) N-bromosuccinimide, 2.) tetra-n-butylammonium bromide, tetra-n-butylammonium fluoride / 1.) carbon tetrachloride, reflux, 25 min., 2.) THF, r.t., 80 min.

8: 37 percent / CHCl₃ / 1 h / Ambient temperature

9: 43.1 percent / sodium borohydride / tetrahydrofuran; methanol / 0.17 h / Ambient temperature

10: 36 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / Heating

11: 1.) benzene, ethanol, irradiation, 2.5 min., 0 degC, 2.) reflux, 1 h

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; dihydrogen peroxide; sodium acetate; lithium; ammonium chloride; toluene-4-sulfonic acid; pyridinium chlorochromate; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; ammonia; dimethyl sulfoxide;
DOI:10.1248/cpb.32.3866

Reference yield:

: 66875-21-6
(20S)-(20-Methyl-5-pregnen-1α,3β,21-triol)-1α,3β-diacetat

: 95270-41-0
(22E,24R)-1α,24-dihydroxy-22-dehydrovitamin D₃

Guidance literature:: Multi-step reaction with 7 steps

1: 82 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 1 h / Ambient temperature

2: 81 percent / dimethylsulfoxide / 72 h / 95 °C

3: 1.) N-bromosuccinimide, 2.) tetra-n-butylammonium bromide, tetra-n-butylammonium fluoride / 1.) carbon tetrachloride, reflux, 25 min., 2.) THF, r.t., 80 min.

4: 37 percent / CHCl₃ / 1 h / Ambient temperature

5: 43.1 percent / sodium borohydride / tetrahydrofuran; methanol / 0.17 h / Ambient temperature

6: 36 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / Heating

7: 1.) benzene, ethanol, irradiation, 2.5 min., 0 degC, 2.) reflux, 1 h

With sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; chloroform; dimethyl sulfoxide;
DOI:10.1248/cpb.32.3866