(1R,3S,5Z)-5-[(2E)-2-[(1S,3aS,7aR)-1-(4-hydroxy-4-methylpentyl)-3a,7a-dimethyl-1,2,3,5,6,7-hexahydroinden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

Base Information

• Chemical Name: (1R,3S,5Z)-5-[(2E)-2-[(1S,3aS,7aR)-1-(4-hydroxy-4-methylpentyl)-3a,7a-dimethyl-1,2,3,5,6,7-hexahydroinden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
• CAS No.: 141300-55-2
• Molecular Formula: C26H42 O3
• Molecular Weight: 402.618
• Mol file: 141300-55-2.mol

Synonyms:1,25-(OH)2-norD3;1,25-dihydroxy-21-norvitamin D3

Chemical Property of (1R,3S,5Z)-5-[(2E)-2-[(1S,3aS,7aR)-1-(4-hydroxy-4-methylpentyl)-3a,7a-dimethyl-1,2,3,5,6,7-hexahydroinden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

Chemical Property:

• Vapor Pressure: 2.58E-14mmHg at 25°C
• Boiling Point: 548.4°Cat760mmHg
• Flash Point: 233.3°C
• PSA: 60.69000
• Density: 1.07g/cm³
• LogP: 5.45870
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 402.31339520
• Heavy Atom Count: 29
• Complexity: 688

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC(=CC=C3CC(CC(C3=C)O)O)C1(CCC2CCCC(C)(C)O)C
• Isomeric SMILES: C[C@]12CCC/C(=C\C=C/3\C[C@H](C[C@@H](C3=C)O)O)/[C@@]1(CC[C@@H]2CCCC(C)(C)O)C

Technology Process of (1R,3S,5Z)-5-[(2E)-2-[(1S,3aS,7aR)-1-(4-hydroxy-4-methylpentyl)-3a,7a-dimethyl-1,2,3,5,6,7-hexahydroinden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

There total 15 articles about (1R,3S,5Z)-5-[(2E)-2-[(1S,3aS,7aR)-1-(4-hydroxy-4-methylpentyl)-3a,7a-dimethyl-1,2,3,5,6,7-hexahydroinden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-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: 18.0%

1α,3β,25-trihydroxy-21-norcholesta-5,7-diene (141300-65-4) → 1alpha,25-Dihydroxy-21-norvitamin D3 (141300-55-2)

Guidance literature:

In ethanol; at 0 ℃; for 0.0833333h; Irradiation;

DOI:10.1248/cpb.40.648

Reference yield:

1α,3β-dihydroxy-androst-5-en-17-one (20998-18-9) → 1alpha,25-Dihydroxy-21-norvitamin D3 (141300-55-2)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) t-BuOK, 3.) pyridine, 4-dimethylaminopyridine

2: 66 percent / diethylaluminum chloride / CH₂Cl₂; hexane / 24 h / Ambient temperature

3: H₂ / 5percent Pt/C / ethyl acetate / 1.5 h / Ambient temperature

4: 85percent KOH / methanol / a) reflux, 6 h, b) RT, 14 h

5: iso-Pr₂NEt / tetrahydrofuran; dimethylformamide / 14 h / 45 °C

6: LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

7: pyridine / 14 h / Ambient temperature

8: LiBr / tetrahydrofuran / 20 h / 50 °C

9: 1.) n-BuLi / 1.) THF, n-hexane, 4 deg C, 2 h, 2.) THF, n-hexane, 4 deg C, 1 h

10: 83 percent / CH₃I, H₂O / acetone / 20 h / Heating

11: 60 percent / tetrahydrofuran / 0.5 h / Ambient temperature

12: 86 percent / 4-dimethylaminopyridine, pyridine / 49 h / Ambient temperature

13: 1.) NBS, NaHCO3, 2.) γ-collidine

14: 34 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

15: 18 percent / ethanol / 0.08 h / 0 °C / Irradiation

With pyridine; 2,4,6-trimethyl-pyridine; dmap; potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; potassium tert-butylate; water; hydrogen; diethylaluminium chloride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; lithium bromide; methyl iodide; platinum on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.40.648

Reference yield:

1α,3β-diacetoxy-21-norpregna-5,17(20)-diene (141300-56-3) → 1alpha,25-Dihydroxy-21-norvitamin D3 (141300-55-2)

Guidance literature:

Multi-step reaction with 14 steps

1: 66 percent / diethylaluminum chloride / CH₂Cl₂; hexane / 24 h / Ambient temperature

2: H₂ / 5percent Pt/C / ethyl acetate / 1.5 h / Ambient temperature

3: 85percent KOH / methanol / a) reflux, 6 h, b) RT, 14 h

4: iso-Pr₂NEt / tetrahydrofuran; dimethylformamide / 14 h / 45 °C

5: LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

6: pyridine / 14 h / Ambient temperature

7: LiBr / tetrahydrofuran / 20 h / 50 °C

8: 1.) n-BuLi / 1.) THF, n-hexane, 4 deg C, 2 h, 2.) THF, n-hexane, 4 deg C, 1 h

9: 83 percent / CH₃I, H₂O / acetone / 20 h / Heating

10: 60 percent / tetrahydrofuran / 0.5 h / Ambient temperature

11: 86 percent / 4-dimethylaminopyridine, pyridine / 49 h / Ambient temperature

12: 1.) NBS, NaHCO3, 2.) γ-collidine

13: 34 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

14: 18 percent / ethanol / 0.08 h / 0 °C / Irradiation

With pyridine; 2,4,6-trimethyl-pyridine; dmap; potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; water; hydrogen; diethylaluminium chloride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; lithium bromide; methyl iodide; platinum on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.40.648

upstream raw materials:

1α,3β,25-trihydroxy-21-norcholesta-5,7-diene

1α,3β-dihydroxy-androst-5-en-17-one

1α,3β-dihydroxy-21,27-bisnorcholest-5-en-25-one

1α,3β,25-trihydroxy-21-norcholest-5-ene

Refernces