25-ketovitamin D₃

Base Information

• Chemical Name: 25-ketovitamin D₃
• CAS No.: 77531-55-6
• Molecular Formula: C₂₆H₄₀O₂
• Molecular Weight: 384.602
• Mol file: 77531-55-6.mol

Synonyms:25-ketovitamin D₃

Chemical Property of 25-ketovitamin D₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 25-ketovitamin D₃

There total 16 articles about 25-ketovitamin 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: 79.0%

25,25-(ethylenedioxy)-27-norvitamin D3 triisopropylsilyl ether (100928-11-8) → 25-ketovitamin D3 (77531-55-6)

Guidance literature:

With AG 50W-X₄(resin); In methanol; for 20h; Ambient temperature;

DOI:10.1021/jo00358a019

Reference yield:

(4R,7aR)-1-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-4-((R,Z)-1-hydroxy-2-((S)-5-hydroxy-2-methylenecyclohexylidene)ethyl)-7a-methyloctahydro-1H-inden-4-ol (84985-78-4) → 25-ketovitamin D3 (77531-55-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 83.3 percent / imidazole / dimethylformamide / 10 h / Ambient temperature

2: 1.) Pb(OAc)4, 2.) NaAlH₂(OCH₂CH₂OCH₃)2 / 1.) CH₂Cl₂, -15 deg C, 15 min, 2.) toluene, RT, 2 h

3: 93 percent / imidazole / CH₂Cl₂; dimethylformamide / 1.) RT, 15 h, 2.) 45 deg C, 20 h, 3.) 80 deg C, 6 h

4: 1.) ozone, 2.) NaBH₄ / 1.) MeOH, pyridine, CH₂Cl₂, -78 deg C, 1 h, 2.) RT, 12 h

5: 95 percent / pyridine / 2 h / 0 °C

6: 94 percent / NaI / acetone / 15 h / Heating

7: 1.) t-BuLi, CuC₂C(CH₃)2OCH₃ / 1.) pentane, -80 deg C, 2.5 h, 2.) Et₂O, -80 deg C, 15 min

8: 48percent aq. HF / acetonitrile / 3 h

9: 80 percent / p-toluenesulfonic acid / 24 h / Ambient temperature

10: 90 percent / pyridinium dichromate, pyridinium p-toluenesulfonate / CH₂Cl₂ / 4.5 h / Ambient temperature

11: 1.) n-BuLi / 1.) hexane, THF, -70 deg C, 30 min, 2.) THF, -70 deg C, 1 h

12: 79 percent / AG 50W-X₄(resin) / methanol / 20 h / Ambient temperature

With pyridine; 1H-imidazole; lead(IV) acetate; sodium tetrahydroborate; dipyridinium dichromate; n-butyllithium; AG 50W-X₄(resin); hydrogen fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; ozone; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium iodide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo00358a019

Reference yield:

(1R,3aR,4S,7aR)-7a-methyl-1-<(2E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl>-octahydro-1H-inden-4-ol (55812-82-3,63730-57-4,63730-58-5,102281-42-5) → 25-ketovitamin D3 (77531-55-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 93 percent / imidazole / CH₂Cl₂; dimethylformamide / 1.) RT, 15 h, 2.) 45 deg C, 20 h, 3.) 80 deg C, 6 h

2: 1.) ozone, 2.) NaBH₄ / 1.) MeOH, pyridine, CH₂Cl₂, -78 deg C, 1 h, 2.) RT, 12 h

3: 95 percent / pyridine / 2 h / 0 °C

4: 94 percent / NaI / acetone / 15 h / Heating

5: 1.) t-BuLi, CuC₂C(CH₃)2OCH₃ / 1.) pentane, -80 deg C, 2.5 h, 2.) Et₂O, -80 deg C, 15 min

6: 48percent aq. HF / acetonitrile / 3 h

7: 80 percent / p-toluenesulfonic acid / 24 h / Ambient temperature

8: 90 percent / pyridinium dichromate, pyridinium p-toluenesulfonate / CH₂Cl₂ / 4.5 h / Ambient temperature

9: 1.) n-BuLi / 1.) hexane, THF, -70 deg C, 30 min, 2.) THF, -70 deg C, 1 h

10: 79 percent / AG 50W-X₄(resin) / methanol / 20 h / Ambient temperature

With pyridine; 1H-imidazole; sodium tetrahydroborate; dipyridinium dichromate; n-butyllithium; AG 50W-X₄(resin); hydrogen fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; ozone; sodium iodide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo00358a019

upstream raw materials:

(R)-4-Methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-[(R)-1-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-butyl]-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexanol

25,25-(ethylenedioxy)-27-norvitamin D₃ triisopropylsilyl ether

(1R,3aR,4S,7aR)-7a-methyl-1-<(2E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl>-octahydro-1H-inden-4-ol

8β-hydroxy-de-A,B-27-norcholestan-25-one

Downstream raw materials:

3-epi-25-hydroxyvitamin D₃