Δ²²,22E,19-nor-24,24-dihomo-26,27-dihomo-1α,25-dihydroxyvitamin D3

Base Information

• Chemical Name: Δ²²,22E,19-nor-24,24-dihomo-26,27-dihomo-1α,25-dihydroxyvitamin D3
• CAS No.: 142777-81-9
• Molecular Formula: C₃₀H₅₀O₃
• Molecular Weight: 458.725
• Mol file: 142777-81-9.mol

Synonyms:

Chemical Property of Δ²²,22E,19-nor-24,24-dihomo-26,27-dihomo-1α,25-dihydroxyvitamin D3

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Δ²²,22E,19-nor-24,24-dihomo-26,27-dihomo-1α,25-dihydroxyvitamin D3

There total 14 articles about Δ²²,22E,19-nor-24,24-dihomo-26,27-dihomo-1α,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:

(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-1-((E)-(R)-7-ethyl-1-methyl-7-triethylsilanyloxy-non-2-enyl)-7a-methyl-octahydro-indene (142777-80-8) → Δ22,22E,19-nor-24,24-dihomo-26,27-dihomo-1α,25-dihydroxyvitamin D3 (142777-81-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 55 ℃; Yield given;

DOI:10.1016/S0040-4039(00)79565-7

Reference yield:

5-Chlorovaleroyl chloride (1575-61-7) → Δ22,22E,19-nor-24,24-dihomo-26,27-dihomo-1α,25-dihydroxyvitamin D3 (142777-81-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 84 percent / diethyl ether; tetrahydrofuran / 2 h / Ambient temperature

2: 92 percent / t-BuOK / dimethylformamide / 16 h / Ambient temperature

3: 67 percent / 3-chloroperbenzoic acid (mCPBA) / CH₂Cl₂ / 2 h / Ambient temperature

4: 99 percent / TEA / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 1) LDA / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 1 h

6: pyridine, DMAP / 16 h / 4 °C

7: 5percent Na/Hg, Na₂HPO₄ / tetrahydrofuran; methanol

8: Bu₄NF / tetrahydrofuran / 55 °C

With pyridine; dmap; disodium hydrogenphosphate; sodium amalgam; TEA; potassium tert-butylate; tetrabutyl ammonium fluoride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)79565-7

Reference yield:

1-chloro-5-ethylheptan-5-ol (31848-92-7) → Δ22,22E,19-nor-24,24-dihomo-26,27-dihomo-1α,25-dihydroxyvitamin D3 (142777-81-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / t-BuOK / dimethylformamide / 16 h / Ambient temperature

2: 67 percent / 3-chloroperbenzoic acid (mCPBA) / CH₂Cl₂ / 2 h / Ambient temperature

3: 99 percent / TEA / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 1) LDA / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 1 h

5: pyridine, DMAP / 16 h / 4 °C

6: 5percent Na/Hg, Na₂HPO₄ / tetrahydrofuran; methanol

7: Bu₄NF / tetrahydrofuran / 55 °C

With pyridine; dmap; disodium hydrogenphosphate; sodium amalgam; TEA; potassium tert-butylate; tetrabutyl ammonium fluoride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)79565-7

upstream raw materials:

(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-1-((E)-(R)-7-ethyl-1-methyl-7-triethylsilanyloxy-non-2-enyl)-7a-methyl-octahydro-indene

5-Chlorovaleroyl chloride

1-chloro-5-ethylheptan-5-ol

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol