26,27-trimethylene-1,25-dihydroxyvitamin D₃

Base Information

• Chemical Name: 26,27-trimethylene-1,25-dihydroxyvitamin D₃
• CAS No.: 114694-10-9
• Molecular Formula: C₂₉H₄₆O₃
• Molecular Weight: 442.682
• Mol file: 114694-10-9.mol

Synonyms:

Chemical Property of 26,27-trimethylene-1,25-dihydroxyvitamin D₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 26,27-trimethylene-1,25-dihydroxyvitamin D₃

There total 20 articles about 26,27-trimethylene-1,25-dihydroxyvitamin D₃ 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:

1-(2'-hydroxyethyl)-1-cyclopentanol (73089-93-7) → 26,27-trimethylene-1,25-dihydroxyvitamin D3 (114694-10-9)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / 20 h / 4 °C

2: potassium tert-butoxide / dimethylformamide / Ambient temperature; overnight

3: 80-85percent 3-chloroperbenzoic acid (MCPBA) / CH₂Cl₂ / 2 h

4: imidazole / dimethylformamide / 2 h / Ambient temperature

5: 1.) LDA, 1,10-phenanthroline / 1.) a.) THF, hexane, -75 deg C, 30 min, b.) -21 deg C, 15 min, 2.) -20 to -10 deg C, 3.5 h

6: 1.) Na₂HPO₄, 2.) 5percent sodium amalgam / 1.) methanol, THF, RT, 30 min, 2.) 5 deg C, 3 h

7: tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 50 °C

With pyridine; 1H-imidazole; disodium hydrogenphosphate; sodium amalgam; 1,10-Phenanthroline; potassium tert-butylate; tetrabutyl ammonium fluoride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00250a009

Reference yield:

hydroxybisnorcholenic acid (566-77-8) → 26,27-trimethylene-1,25-dihydroxyvitamin D3 (114694-10-9)

Guidance literature:

Multi-step reaction with 15 steps

1: H₂SO₄

2: imidazole / dimethylformamide

4: 1.) benzene, ethyl ether, irradiation, 40 min, 2.) ethanol, reflux, 3 h

5: pyridine / 20 h / 4 °C

6: potassium bicarbonate / CH₂Cl₂ / 24 h / 55 °C

7: 12.5 mg / 3.0 M tert-butyl hydroperoxide in toluene, selenium dioxide, pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

8: 6 mg / 0.25 h / 55 °C

9: 96 percent / 0.1 N methanolic KOH / diethyl ether / 1.5 h / Ambient temperature

10: 98 percent / imidazole / dimethylformamide / 0.25 h / 55 °C

11: 91 percent / lithium aluminum hydride / tetrahydrofuran / 0.25 h / 0 °C

12: 98 percent / pyridine / 22 h / 5 °C

13: 1.) LDA, 1,10-phenanthroline / 1.) a.) THF, hexane, -75 deg C, 30 min, b.) -21 deg C, 15 min, 2.) -20 to -10 deg C, 3.5 h

14: 1.) Na₂HPO₄, 2.) 5percent sodium amalgam / 1.) methanol, THF, RT, 30 min, 2.) 5 deg C, 3 h

15: tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 50 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; potassium hydroxide; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; selenium(IV) oxide; 1,10-Phenanthroline; sulfuric acid; tetrabutyl ammonium fluoride; potassium hydrogencarbonate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00250a009

Reference yield:

methyl 3β-hydroxy-23-bisnorchol-5-en-22-oate (10527-79-4) → 26,27-trimethylene-1,25-dihydroxyvitamin D3 (114694-10-9)

Guidance literature:

Multi-step reaction with 14 steps

1: imidazole / dimethylformamide

3: 1.) benzene, ethyl ether, irradiation, 40 min, 2.) ethanol, reflux, 3 h

4: pyridine / 20 h / 4 °C

5: potassium bicarbonate / CH₂Cl₂ / 24 h / 55 °C

6: 12.5 mg / 3.0 M tert-butyl hydroperoxide in toluene, selenium dioxide, pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

7: 6 mg / 0.25 h / 55 °C

8: 96 percent / 0.1 N methanolic KOH / diethyl ether / 1.5 h / Ambient temperature

9: 98 percent / imidazole / dimethylformamide / 0.25 h / 55 °C

10: 91 percent / lithium aluminum hydride / tetrahydrofuran / 0.25 h / 0 °C

11: 98 percent / pyridine / 22 h / 5 °C

12: 1.) LDA, 1,10-phenanthroline / 1.) a.) THF, hexane, -75 deg C, 30 min, b.) -21 deg C, 15 min, 2.) -20 to -10 deg C, 3.5 h

13: 1.) Na₂HPO₄, 2.) 5percent sodium amalgam / 1.) methanol, THF, RT, 30 min, 2.) 5 deg C, 3 h

14: tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 50 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; potassium hydroxide; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; selenium(IV) oxide; 1,10-Phenanthroline; tetrabutyl ammonium fluoride; potassium hydrogencarbonate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00250a009

upstream raw materials:

1-(2'-hydroxyethyl)-1-cyclopentanol

hydroxybisnorcholenic acid

methyl 3β-hydroxy-23-bisnorchol-5-en-22-oate

3β-hydroxy-22,23-dinor-5,7-choladienic acid methyl ester