(20S)-3β-(tert-butyldimethylsilyloxy)-22-phenylsulfonyl-23,24-dinorchola-5,7-diene

Base Information

• Chemical Name: (20S)-3β-(tert-butyldimethylsilyloxy)-22-phenylsulfonyl-23,24-dinorchola-5,7-diene
• CAS No.: 249564-48-5
• Molecular Formula: C₃₄H₅₂O₃SSi
• Molecular Weight: 568.937
• Mol file: 249564-48-5.mol

Synonyms:(20S)-3β-(tert-butyldimethylsilyloxy)-22-phenylsulfonyl-23,24-dinorchola-5,7-diene

Chemical Property of (20S)-3β-(tert-butyldimethylsilyloxy)-22-phenylsulfonyl-23,24-dinorchola-5,7-diene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (20S)-3β-(tert-butyldimethylsilyloxy)-22-phenylsulfonyl-23,24-dinorchola-5,7-diene

There total 1 articles about (20S)-3β-(tert-butyldimethylsilyloxy)-22-phenylsulfonyl-23,24-dinorchola-5,7-diene 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: 97.6%

3β-hydroxy-23,24-bisnorchola-5,7-dien-22-yl phenyl sulfone (104729-36-4) + tert-butyldimethylsilyl chloride (18162-48-6) → (20S)-3β-(tert-butyldimethylsilyloxy)-22-phenylsulfonyl-23,24-dinorchola-5,7-diene (249564-48-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1016/S0039-128X(99)00057-4

Reference yield: 83.4%

(2R)-2,3-dihydroxy-3-methylbutan-1-yl p-toluenesulfonate (77522-15-7) + (20S)-3β-(tert-butyldimethylsilyloxy)-22-phenylsulfonyl-23,24-dinorchola-5,7-diene (249564-48-5) → (20S,22ξ,24R)-3β-(tert-butyldimethylsilyloxy)-22-phenylsulfonylcholesta-5,7-diene-24,25-diol (249564-50-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -30 ℃; for 2h;

DOI:10.1016/S0039-128X(99)00057-4

Reference yield:

(20S)-3β-(tert-butyldimethylsilyloxy)-22-phenylsulfonyl-23,24-dinorchola-5,7-diene (249564-48-5) → (5Z,7E)-(3S,24R)-24,25-dihydroxy-9,10-secocholesta-5,7,10(19)-trien-3β-yl β-D-glycopyranuronic acid (203737-06-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 83.4 percent / BuLi / tetrahydrofuran / 2 h / -30 °C

2.1: 73.8 percent / 5 percent Na-Hg; Na₂HPO₄ / tetrahydrofuran; methanol / 3.5 h / 20 °C

3.1: 92 percent / pyridine / 4 h / 20 °C

4.1: 83.2 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

5.1: 47.1 percent / Ag₂CO₃ / CHCl₃ / 2.5 h / 20 °C

6.1: diethyl ether / 0 °C / UV-irradiation

6.2: 15.8 percent / ethanol / 25 h / 20 - 65 °C

7.1: 84 percent / NaOH / methanol / 24 h / 20 °C

With pyridine; sodium hydroxide; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; tetrabutyl ammonium fluoride; silver carbonate; In tetrahydrofuran; methanol; diethyl ether; chloroform; 1.1: Alkylation / 2.1: Reduction / 3.1: Acetylation / 4.1: Desilylation / 5.1: Glycosidation / 6.1: Rearrangement / 6.2: Rearrangement / 7.1: Hydrolysis;

DOI:10.1016/S0039-128X(99)00057-4

upstream raw materials:

3β-hydroxy-23,24-bisnorchola-5,7-dien-22-yl phenyl sulfone

tert-butyldimethylsilyl chloride

Downstream raw materials:

(20S,22ξ,24R)-3β-(tert-butyldimethylsilyloxy)-22-phenylsulfonylcholesta-5,7-diene-24,25-diol

(5Z,7E)-(3S,24R)-24,25-dihydroxy-9,10-secocholesta-5,7,10(19)-trien-3β-yl β-D-glycopyranuronic acid

methyl {[(5Z,7E)-(3S,24R)-24-acetoxy-25-hydroxy-9,10-secocholesta-5,7,10(19)-trien-3β-yl]-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate