3β-tert-butyldimethylsilyl-1α-tert-butyldimethylsilyloxy-25-trimethylsilyloxy-19-norvitamin D₃

Base Information

• Chemical Name: 3β-tert-butyldimethylsilyl-1α-tert-butyldimethylsilyloxy-25-trimethylsilyloxy-19-norvitamin D₃
• CAS No.: 599165-21-6
• Molecular Formula: C₄₂H₈₀O₃Si₃
• Molecular Weight: 717.352
• Mol file: 599165-21-6.mol

Synonyms:3β-tert-butyldimethylsilyl-1α-tert-butyldimethylsilyloxy-25-trimethylsilyloxy-19-norvitamin D₃

Chemical Property of 3β-tert-butyldimethylsilyl-1α-tert-butyldimethylsilyloxy-25-trimethylsilyloxy-19-norvitamin D₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3β-tert-butyldimethylsilyl-1α-tert-butyldimethylsilyloxy-25-trimethylsilyloxy-19-norvitamin D₃

There total 48 articles about 3β-tert-butyldimethylsilyl-1α-tert-butyldimethylsilyloxy-25-trimethylsilyloxy-19-norvitamin 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: 62.0%

(1R,7aR)-1-((R)-1,5-Dimethyl-5-trimethylsilanyloxy-hexyl)-7a-methyl-octahydro-inden-4-one (81506-41-4,126714-28-1) + [(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (81522-68-1) → 3β-tert-butyldimethylsilyl-1α-tert-butyldimethylsilyloxy-25-trimethylsilyloxy-19-norvitamin D3 (599165-21-6)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -20 - 50 ℃;

DOI:10.1080/00397910500503645

Reference yield: 43.0%

(1R,3aR,7aR)-1-{(1R)-1,5-dimethyl-5-[(trimethylsilyl)oxy]hexyl}-7a-methyloctahydro-4H-inden-4-one (81506-41-4) + [(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (81522-68-1) → 3β-tert-butyldimethylsilyl-1α-tert-butyldimethylsilyloxy-25-trimethylsilyloxy-19-norvitamin D3 (599165-21-6)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -20 - 50 ℃; for 0.269722h; Product distribution / selectivity;

Reference yield:

(1S,3aS,4S,7aS)-1-tert-Butoxy-7a-methyl-5-oxo-octahydro-indene-4-carboxylic acid (53702-06-0) → 3β-tert-butyldimethylsilyl-1α-tert-butyldimethylsilyloxy-25-trimethylsilyloxy-19-norvitamin D3 (599165-21-6)

Guidance literature:

Multi-step reaction with 20 steps

1: NaBH₄ / ethanol

2: 96 percent / diethyl ether; tetrahydrofuran / Heating

3: pyridine / 0 °C

4: NaI / dimethylformamide; pyridine / 100 °C

5: hydrogen / Pd/C / ethanol / 25 °C

6: EtONa / ethanol / 25 °C

7: 95 percent / m-CPBA / CH₂Cl₂ / 25 °C

8: 98 percent / trimethylsilyl iodide / CCl₄ / 25 °C

9: 95 percent / PCC / CH₂Cl₂ / 25 °C

10: EtONa / ethanol / 25 °C

11: tetrahydrofuran / 25 °C

12: 96 percent / pyridine / 25 °C

13: 88 percent / EtAlCl₂ / CH₂Cl₂ / 25 °C

14: 98 percent / hydrogen / Pd/C / ethanol / 25 °C

15: 92 percent / diisobutylaluminum hydride / CH₂Cl₂; toluene / -78 °C

16: 89 percent / tetrahydrofuran / 25 °C

17: 1.) Hg(OAc)2, 2.) NaBH₄ / 1.) THF, H₂O, 2.) 25 deg C

18: PCC / CH₂Cl₂ / 25 °C

19: 98 percent / tetrahydrofuran / 25 °C

20: tetrahydrofuran / 1 h / -78 °C

With sodium tetrahydroborate; trimethylsilyl iodide; mercury(II) diacetate; hydrogen; sodium ethanolate; ethylaluminum dichloride; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; pyridine; tetrachloromethane; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00374a052

upstream raw materials:

(1R,3aR,7aR)-1-{(1R)-1,5-dimethyl-5-[(trimethylsilyl)oxy]hexyl}-7a-methyloctahydro-4H-inden-4-one

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

(1R,3aS,7aR)-(E)-2-{1-[(R)-1,5-dimethyl-5-(trimethylsilanyloxy)hexyl]-7a-methyloctahydroinden-4-ylidenemethyl}-4,4,5,5-tetramethyl[1,3,2]dioxaborolane

(Z)-(3S,5R)-1-bromomethylene-3,5-bis(tert-butyldimethylsilyloxy)-2-methylenecyclohexane

Downstream raw materials:

calcitriol