des-A,B-8β-[(triethylsilyl)oxy]-22-(p-toluenesulfonyloxy)-23,24-dinorcholane

Base Information

• Chemical Name: des-A,B-8β-[(triethylsilyl)oxy]-22-(p-toluenesulfonyloxy)-23,24-dinorcholane
• CAS No.: 189102-18-9
• Molecular Formula: C₂₆H₄₄O₄SSi
• Molecular Weight: 480.784

Synonyms:des-A,B-8β-[(triethylsilyl)oxy]-22-(p-toluenesulfonyloxy)-23,24-dinorcholane

Chemical Property of des-A,B-8β-[(triethylsilyl)oxy]-22-(p-toluenesulfonyloxy)-23,24-dinorcholane

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of des-A,B-8β-[(triethylsilyl)oxy]-22-(p-toluenesulfonyloxy)-23,24-dinorcholane

There total 4 articles about des-A,B-8β-[(triethylsilyl)oxy]-22-(p-toluenesulfonyloxy)-23,24-dinorcholane 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: 99.0%

(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate (66774-80-9,111924-49-3) + triethylsilyl trifluoromethyl sulfonate (79271-56-0) → des-A,B-8β-[(triethylsilyl)oxy]-22-(p-toluenesulfonyloxy)-23,24-dinorcholane (189102-18-9)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.25h;

Reference yield: 85.0%

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol (64190-52-9) + triethylsilyl trifluoromethyl sulfonate (79271-56-0) + p-toluenesulfonyl chloride (98-59-9) → des-A,B-8β-[(triethylsilyl)oxy]-22-(p-toluenesulfonyloxy)-23,24-dinorcholane (189102-18-9)

Guidance literature:

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol; p-toluenesulfonyl chloride; With pyridine;

triethylsilyl trifluoromethyl sulfonate; With 2,6-dimethylpyridine; Further stages.;

DOI:10.1016/j.tetlet.2004.04.118

Reference yield:

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol (64190-52-9) → des-A,B-8β-[(triethylsilyl)oxy]-22-(p-toluenesulfonyloxy)-23,24-dinorcholane (189102-18-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Py / 1.) -25 deg C, 3.5 h, 2.) 0 deg C, 20 h.

2: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

With pyridine; 2,6-dimethylpyridine; In dichloromethane;

DOI:10.1021/jo970049w

upstream raw materials:

(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate

triethylsilyl trifluoromethyl sulfonate

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

p-toluenesulfonyl chloride

Downstream raw materials:

4-[(R)-2-((1R,3aR,4S,7aR)-7a-Methyl-4-triethylsilanyloxy-octahydro-inden-1-yl)-propyl]-1-phenyl-1H-[1,2,3]triazole

4-((R)-2-{(1R,3aS,7aR)-4-[2-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-1-phenyl-1H-[1,2,3]triazole

1,4-bis-[2-(4-{2-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene}-7a-methyl-octahydro-inden-1-yl)-propyl]-1H-[1,2,3]triazole

(20R)-2-methylene-19-nor-22-dimethyl-1α,25-dihydroxyvitamin D₃

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