24-fluoro-25-hydroxyvitamin D₃

Base Information

• Chemical Name: 24-fluoro-25-hydroxyvitamin D₃
• CAS No.: 72342-07-5
• Molecular Formula: C₂₇H₄₃FO₂
• Molecular Weight: 418.636
• Mol file: 72342-07-5.mol

Synonyms:

Chemical Property of 24-fluoro-25-hydroxyvitamin D₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 24-fluoro-25-hydroxyvitamin D₃

There total 16 articles about 24-fluoro-25-hydroxyvitamin 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:

3β-hydroxy-5-cholenoic acid (5255-17-4) → 24-fluoro-25-hydroxyvitamin D3 (72342-07-5)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) p-TsOH, 2.) LiAlH₄ / 1.) CH₂Cl₂, 0 deg C, 4 h, 2.) THF, 60 deg C, 4 h

2: pyridine / CH₂Cl₂ / 24 h / Ambient temperature

3: 48 percent / 18-crown-6 / dimethylformamide / 3 h / 60 - 80 °C

4: 63 percent / KOH / H₂O; ethanol / 48 h / 140 °C

5: 79 percent / CH₂Cl₂

6: 1.) n-BuLi, dicyclohexylamine, 2.) I₂ / tetrahydrofuran / 1.) -78 deg C, 10 min -> room temperature, 5 min, 2.) -78 deg C, 5 min

7: 1.) silver trifluoroacetate, silver oxide, 2.) KOH / 1.) CH₃CN, Et₂O, room temperature, 20 h, 2.) THF, CH₃OH, room temperature, 16 h

8: CH₂Cl₂ / 0 °C

9: 68 percent / pyridine / CH₂Cl₂ / 4 h / Ambient temperature

10: 293 mg / 18-crown-6, KF / dimethylformamide / 15 h / 70 °C

11: 73 percent

12: 2.) pyridine / 1.) Et₂O, room temperature, 20 min, 2.) CH₂Cl₂, room temperature, 12 h

13: 18 percent / 1.) NBS, 2.) s-collidine / 1.) CCl₄, reflux, 45 min, 2.) xylene, reflux, 10 min

14: 2.5 mg / KOH / tetrahydrofuran; methanol / 16 h / Ambient temperature

15: 0.52 mg / benzene; ethanol / irradiation, 2.5 min -> reflux, 1 h

With pyridine; 2,4,6-trimethyl-pyridine; potassium fluoride; potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; 18-crown-6 ether; iodine; silver trifluoroacetate; toluene-4-sulfonic acid; N-cyclohexyl-cyclohexanamine; silver(l) oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

Reference yield:

3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-ol (66414-43-5) → 24-fluoro-25-hydroxyvitamin D3 (72342-07-5)

Guidance literature:

Multi-step reaction with 14 steps

1: pyridine / CH₂Cl₂ / 24 h / Ambient temperature

2: 48 percent / 18-crown-6 / dimethylformamide / 3 h / 60 - 80 °C

3: 63 percent / KOH / H₂O; ethanol / 48 h / 140 °C

4: 79 percent / CH₂Cl₂

5: 1.) n-BuLi, dicyclohexylamine, 2.) I₂ / tetrahydrofuran / 1.) -78 deg C, 10 min -> room temperature, 5 min, 2.) -78 deg C, 5 min

6: 1.) silver trifluoroacetate, silver oxide, 2.) KOH / 1.) CH₃CN, Et₂O, room temperature, 20 h, 2.) THF, CH₃OH, room temperature, 16 h

7: CH₂Cl₂ / 0 °C

8: 68 percent / pyridine / CH₂Cl₂ / 4 h / Ambient temperature

9: 293 mg / 18-crown-6, KF / dimethylformamide / 15 h / 70 °C

10: 73 percent

11: 2.) pyridine / 1.) Et₂O, room temperature, 20 min, 2.) CH₂Cl₂, room temperature, 12 h

12: 18 percent / 1.) NBS, 2.) s-collidine / 1.) CCl₄, reflux, 45 min, 2.) xylene, reflux, 10 min

13: 2.5 mg / KOH / tetrahydrofuran; methanol / 16 h / Ambient temperature

14: 0.52 mg / benzene; ethanol / irradiation, 2.5 min -> reflux, 1 h

With pyridine; 2,4,6-trimethyl-pyridine; potassium fluoride; potassium hydroxide; N-Bromosuccinimide; n-butyllithium; 18-crown-6 ether; iodine; silver trifluoroacetate; N-cyclohexyl-cyclohexanamine; silver(l) oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

Reference yield:

3β-acetoxy-24-fluorocholest-5-en-25-ol (72349-23-6) → 24-fluoro-25-hydroxyvitamin D3 (72342-07-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 18 percent / 1.) NBS, 2.) s-collidine / 1.) CCl₄, reflux, 45 min, 2.) xylene, reflux, 10 min

2: 2.5 mg / KOH / tetrahydrofuran; methanol / 16 h / Ambient temperature

3: 0.52 mg / benzene; ethanol / irradiation, 2.5 min -> reflux, 1 h

With 2,4,6-trimethyl-pyridine; potassium hydroxide; N-Bromosuccinimide; In tetrahydrofuran; methanol; ethanol; benzene;

upstream raw materials:

(3S,9S,10R,13R,14R,17R)-17-((R)-4-Fluoro-5-hydroxy-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

3β-hydroxy-5-cholenoic acid

3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-ol

methyl 24-fluoro-3β-hydroxychol-5-ene-24-carboxylate