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

Base Information

• Chemical Name: (1S,3R,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(E,2R)-5,5,6-trimethylhept-3-en-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
• CAS No.: 104211-64-5
• Molecular Formula: C₂₉H₄₆O₂
• Molecular Weight: 426.683
• Mol file: 104211-64-5.mol

Synonyms:1-hydroxy-24,24-dimethyl-22-dehydrovitamin D3;OH-DMDH-D3

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

Chemical Property:

• Vapor Pressure: 3.33E-14mmHg at 25°C
• Boiling Point: 546.1°Cat760mmHg
• Flash Point: 224.5°C
• PSA: 40.46000
• Density: 1.01g/cm³
• LogP: 7.00190
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 426.349780706
• Heavy Atom Count: 31
• Complexity: 753

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 10 articles about (1S,3R,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(E,2R)-5,5,6-trimethylhept-3-en-2-yl]-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: 23.0%

1α,3β-dihydroxy-24,24-dimethylcholesta-5,7,22E-triene (104211-63-4) → 1α-hydroxy-24,24-dimethyl-22E-dehydrovitamin D3 (104211-64-5)

Guidance literature:

In ethanol; benzene; Irradiation; 0 deg C, 5 min, reflux, 1 h;

DOI:10.1248/cpb.33.4815

Reference yield:

22ξ-hydroxy-1α,3β-bismethoxymethoxy-26,27-dinorergosta-5,23-diene (104211-56-5) → 1α-hydroxy-24,24-dimethyl-22E-dehydrovitamin D3 (104211-64-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 88 percent / propionic acid / xylene / 2 h / Heating

2: 130 mg / LiAlH₄ / tetrahydrofuran / 16 h / Ambient temperature

3: 145 mg / pyridine / 1.5 h / Ambient temperature

4: 52 mg / lithium triethylborohydride / tetrahydrofuran / 0.5 h / 60 °C

5: 87 percent / 4-dimethylaminopyridine / pyridine / 17 h / Ambient temperature

6: N-bromosuccinimide / CCl₄ / 0.33 h / Heating

7: 1.) tetra-n-butylammonium bromide, 2.) tetra-n-butylammonium fluoride / tetrahydrofuran / 1.) room temperature, 50 min, 2.) room temperature, 30 min

8: 5.2 mg / 5percent KOH-MeOH / tetrahydrofuran / 14 h / Ambient temperature

9: 23 percent / benzene; ethanol / Irradiation; 0 deg C, 5 min, reflux, 1 h

With dmap; potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; lithium triethylborohydride; propionic acid; In tetrahydrofuran; pyridine; tetrachloromethane; ethanol; xylene; benzene;

DOI:10.1248/cpb.33.4815

Reference yield:

1α,3β-dihydroxy-24,24-dimethylcholesta-5,22E-diene → 1α-hydroxy-24,24-dimethyl-22E-dehydrovitamin D3 (104211-64-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / 4-dimethylaminopyridine / pyridine / 17 h / Ambient temperature

2: N-bromosuccinimide / CCl₄ / 0.33 h / Heating

3: 1.) tetra-n-butylammonium bromide, 2.) tetra-n-butylammonium fluoride / tetrahydrofuran / 1.) room temperature, 50 min, 2.) room temperature, 30 min

4: 5.2 mg / 5percent KOH-MeOH / tetrahydrofuran / 14 h / Ambient temperature

5: 23 percent / benzene; ethanol / Irradiation; 0 deg C, 5 min, reflux, 1 h

With dmap; potassium hydroxide; N-Bromosuccinimide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; In tetrahydrofuran; pyridine; tetrachloromethane; ethanol; benzene;

DOI:10.1248/cpb.33.4815

upstream raw materials:

1α,3β-dihydroxy-24,24-dimethylcholesta-5,7,22E-triene

22ξ-hydroxy-1α,3β-bismethoxymethoxy-26,27-dinorergosta-5,23-diene

(E)-(R)-6-((1S,3R,8S,9S,10R,13R,14S,17R)-1,3-Bis-methoxymethoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2,3,3-trimethyl-hept-4-en-1-ol

1α,3β-diacetoxy-24,24-dimethylcholesta-5,22E-diene

Refernces