Dihydrotachysterol3

Base Information

• Chemical Name: Dihydrotachysterol3
• CAS No.: 22481-38-5
• Molecular Formula: C₂₇H₄₆O
• Molecular Weight: 386.662
• UNII: 6SX9EHV767
• DSSTox Substance ID: DTXSID301315542
• Wikidata: Q27265463
• Metabolomics Workbench ID: 35855
• Mol file: 22481-38-5.mol

Synonyms:Dihydrotachysterol3;dihydrotachysterol 3;(5E,7E)-(3S,10S)-9,10-seco-5,7-cholestatrien-3-ol;dihydrotachysterol3 / (5E)-(10S)-10,19-dihydrovitamin D3 / (5E)-(10S)-10,19-dihydrocholecalciferol;LMST03020307;TACHYSTEROL3, DIHYDRO-;DTXSID301315542;9,10-SECO-.DELTA.5,7-CHOLESTADIEN-3-OL;Q27265463;9,10-SECOCHOLESTA-5,7-DIEN-3-OL, (3.BETA.,5E,7E,10.ALPHA.)-;CYCLOHEXANOL, 3-((2E)-2-((1R,3ASR,7AR)-1-((1R)-1,5-DIMETHYLHEXYL)OCTAHYDRO-7A-METHYL-4H-INDEN-4-YLIDENE)ETHENYL)-4-METHYL-, (1S,2E,4S)-

Chemical Property of Dihydrotachysterol3

Chemical Property:

• Vapor Pressure: 4.18E-12mmHg at 25°C
• Boiling Point: 500.3°C at 760 mmHg
• Flash Point: 218.6°C
• PSA: 20.23000
• Density: 0.992g/cm³
• LogP: 7.94490
• XLogP3: 8.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 386.354866087
• Heavy Atom Count: 28
• Complexity: 571

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(CC1=CC=C2CCCC3(C2CCC3C(C)CCCC(C)C)C)O
• Isomeric SMILES: C[C@H]\1CC[C@@H](C/C1=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C)O

Technology Process of Dihydrotachysterol3

There total 16 articles about Dihydrotachysterol3 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:

vitamin D3 (67-97-0) → (3S,5E,7E,10S)-9,10-seco-cholesta-5,7-dien-3-ol (22481-38-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) ozone, 2.) Me₂S / 1.) methanol, -78 deg C, 2.) methanol, RT, 8 h

2: ethylmagnesium bromide / tetrahydrofuran / 2 h / Ambient temperature

3: KOH / dimethylsulfoxide / 0.25 h / Ambient temperature

4: 1.) n-BuLi / 1.) THF, hexane, RT, 5 min, 2.) THF, hexane, RT, 1 h

5: 100 percent / ZnBr₂ / CH₂Cl₂ / 8 h

6: 100 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

7: LiAlH₄, TiCl₃ / diethyl ether; tetrahydrofuran / 1 h / Heating

With potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; titanium(III) chloride; dimethylsulfide; ethylmagnesium bromide; ozone; zinc dibromide; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jo00392a012

Reference yield:

(-)-dihydrocarvone (5524-05-0,619-02-3) → (3S,5E,7E,10S)-9,10-seco-cholesta-5,7-dien-3-ol (22481-38-5)

Guidance literature:

Multi-step reaction with 10 steps

1: PPTS / benzene / 1 h / Heating

2: 1.) ozone, 2.) Me₂S / 1.) methanol, -30 deg C, 2.) methanol, RT, 8 h

3: NaHCO₃, m-CPBA / CH₂Cl₂ / 24 h / Ambient temperature

4: potassium carbonate / methanol; H₂O / 3 h / Ambient temperature

5: NaH / dimethylformamide / 2 h / 0 °C

6: PPTS / acetone; H₂O / 4 h / Heating

7: 1.) n-BuLi / 1.) THF, hexane, RT, 5 min, 2.) THF, hexane, RT, 1 h

8: 100 percent / ZnBr₂ / CH₂Cl₂ / 8 h

9: 100 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

10: LiAlH₄, TiCl₃ / diethyl ether; tetrahydrofuran / 1 h / Heating

With lithium aluminium tetrahydride; n-butyllithium; titanium(III) chloride; dimethylsulfide; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; ozone; 3-chloro-benzenecarboperoxoic acid; zinc dibromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo00392a012

Reference yield:

Grundmann's ketone (66251-18-1) → (3S,5E,7E,10S)-9,10-seco-cholesta-5,7-dien-3-ol (22481-38-5)

Guidance literature:

Multi-step reaction with 6 steps

1: ethylmagnesium bromide / tetrahydrofuran / 2 h / Ambient temperature

2: KOH / dimethylsulfoxide / 0.25 h / Ambient temperature

3: 1.) n-BuLi / 1.) THF, hexane, RT, 5 min, 2.) THF, hexane, RT, 1 h

4: 100 percent / ZnBr₂ / CH₂Cl₂ / 8 h

5: 100 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

6: LiAlH₄, TiCl₃ / diethyl ether; tetrahydrofuran / 1 h / Heating

With potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; titanium(III) chloride; ethylmagnesium bromide; zinc dibromide; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jo00392a012

upstream raw materials:

tachysterol₃

(3S,6S)-1-{(E)-2-[(1R,3aR,4R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-4-methoxy-7a-methyl-octahydro-inden-4-yl]-vinyl}-6-methyl-cyclohexane-1,3-diol

vitamin D₃

(-)-dihydrocarvone

Refernces