(1R,3S,5E)-5-[(2E)-2-[(3aS,7aR)-1-[1-(2-hydroxy-2-methylpropyl)sulfanylpropan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

Base Information

• Chemical Name: (1R,3S,5E)-5-[(2E)-2-[(3aS,7aR)-1-[1-(2-hydroxy-2-methylpropyl)sulfanylpropan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
• CAS No.: 87480-00-0
• Molecular Formula: C₂₆H₄₂O₃S
• Molecular Weight: 434.684
• Mol file: 87480-00-0.mol

Synonyms:1 alpha,25-dihydroxy-23-thiavitamin D3;1,25-dihydroxy-23-thiavitamin D3;1,25-DTVD3

Chemical Property of (1R,3S,5E)-5-[(2E)-2-[(3aS,7aR)-1-[1-(2-hydroxy-2-methylpropyl)sulfanylpropan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

Chemical Property:

• Vapor Pressure: 5.95E-17mmHg at 25°C
• Boiling Point: 601°C at 760 mmHg
• Flash Point: 291°C
• PSA: 85.99000
• Density: 1.11g/cm³
• LogP: 5.26760
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 434.28546637
• Heavy Atom Count: 30
• Complexity: 694

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CSCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C
• Isomeric SMILES: CC(CSCC(C)(C)O)C1CC[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 (1R,3S,5E)-5-[(2E)-2-[(3aS,7aR)-1-[1-(2-hydroxy-2-methylpropyl)sulfanylpropan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

There total 13 articles about (1R,3S,5E)-5-[(2E)-2-[(3aS,7aR)-1-[1-(2-hydroxy-2-methylpropyl)sulfanylpropan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-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:

(20S)-20-methyl-5,16-pregnadien-1α,3β,21-triol 1,3-diacetate (81481-22-3) → 23-thia-1α,25-dihydroxyvitamin D3 (87480-00-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.72 g / H₂ / 5percent Pt/C / ethyl acetate / Ambient temperature

2: 1.70 g / Amberlyst-15 / CH₂Cl₂ / 15 h / Ambient temperature

3: 1.13 g / LiAlH₄ / tetrahydrofuran / 1 h / Heating

4: 74 percent / imidazole, hydroxybenzotriazole / dimethylformamide / 48 h / 65 - 70 °C

5: 71 percent / Me₂AlCl / CH₂Cl₂ / 15 h / Ambient temperature

6: 84 percent / 4,4-dimethylaminopyridine, pyridine / 20 h / Ambient temperature

7: 1.) N-bromosuccinimide, 2.) γ-collidine / 1.) n-hexane, RT, 1.25 h, 2.) xylene, reflux, 1 h

8: K₂CO₃ / ethanol / 21 h / 30 °C

9: 67 mg / pyridine / 0.75 h / Ambient temperature

10: 47 percent / hexamethylphosphoramide (HMPA), NaH / tetrahydrofuran / 4 h / Ambient temperature

11: 1.) EtOH, irradiation, 0 deg C, 4.5 min, 2.) EtOH, reflux, 1.5 h

12: n-Bu₄NF / tetrahydrofuran / 16 h / Ambient temperature

With pyridine; 1H-imidazole; 2,4,6-trimethyl-pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; amberlyst-15; tetrabutyl ammonium fluoride; hydrogen; dimethylaluminum chloride; sodium hydride; potassium carbonate; benzotriazol-1-ol; platinum on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1248/cpb.39.3221

Reference yield:

(17Z)-5,17-pregnadiene-1α,3β-diol diacetate (77308-29-3) → 23-thia-1α,25-dihydroxyvitamin D3 (87480-00-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 89 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 1.72 g / H₂ / 5percent Pt/C / ethyl acetate / Ambient temperature

3: 1.70 g / Amberlyst-15 / CH₂Cl₂ / 15 h / Ambient temperature

4: 1.13 g / LiAlH₄ / tetrahydrofuran / 1 h / Heating

5: 74 percent / imidazole, hydroxybenzotriazole / dimethylformamide / 48 h / 65 - 70 °C

6: 71 percent / Me₂AlCl / CH₂Cl₂ / 15 h / Ambient temperature

7: 84 percent / 4,4-dimethylaminopyridine, pyridine / 20 h / Ambient temperature

8: 1.) N-bromosuccinimide, 2.) γ-collidine / 1.) n-hexane, RT, 1.25 h, 2.) xylene, reflux, 1 h

9: K₂CO₃ / ethanol / 21 h / 30 °C

10: 67 mg / pyridine / 0.75 h / Ambient temperature

11: 47 percent / hexamethylphosphoramide (HMPA), NaH / tetrahydrofuran / 4 h / Ambient temperature

12: 1.) EtOH, irradiation, 0 deg C, 4.5 min, 2.) EtOH, reflux, 1.5 h

13: n-Bu₄NF / tetrahydrofuran / 16 h / Ambient temperature

With pyridine; 1H-imidazole; 2,4,6-trimethyl-pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; amberlyst-15; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; dimethylaluminum chloride; sodium hydride; potassium carbonate; benzotriazol-1-ol; platinum on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1248/cpb.39.3221

Reference yield:

1-((S)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propylsulfanyl)-2-methyl-propan-2-ol (139137-33-0,139239-36-4) → 23-thia-1α,25-dihydroxyvitamin D3 (87480-00-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 16h; Yield given; Ambient temperature;

DOI:10.1248/cpb.39.3221

upstream raw materials:

1-((S)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propylsulfanyl)-2-methyl-propan-2-ol

(20S)-20-Methyl-21-(tetrahydro-2H-pyran-2-yl)oxy-5-pregnen-1α,3β-diol

1α,3β-bis<(tert-butyldimethylsilyl)oxy>-23,24-bisnorchol-5-en-22-ol

1α,3β-bis<(tert-butyldimethylsilyl)oxy>-23,24-bisnorchol-5,7-dien-22-ol

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