3-O-tert-butyldimethylsilyl-17α-hydroxypropargyl-β-estradiolyl 2-phenylquinoline-4-carboxylate

Base Information

• Chemical Name: 3-O-tert-butyldimethylsilyl-17α-hydroxypropargyl-β-estradiolyl 2-phenylquinoline-4-carboxylate
• CAS No.: 959414-78-9
• Molecular Formula: C₄₃H₄₉NO₄Si
• Molecular Weight: 671.952
• Mol file: 959414-78-9.mol

Synonyms:3-O-tert-butyldimethylsilyl-17α-hydroxypropargyl-β-estradiolyl 2-phenylquinoline-4-carboxylate

Chemical Property of 3-O-tert-butyldimethylsilyl-17α-hydroxypropargyl-β-estradiolyl 2-phenylquinoline-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-tert-butyldimethylsilyl-17α-hydroxypropargyl-β-estradiolyl 2-phenylquinoline-4-carboxylate

There total 4 articles about 3-O-tert-butyldimethylsilyl-17α-hydroxypropargyl-β-estradiolyl 2-phenylquinoline-4-carboxylate 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: 95.0%

cinchophen (132-60-5) + 3-(tert-butyldimethylsilyloxy)-17α-(3'-hydroxyprop-1'-ynyl)estradiol (211183-97-0) → 3-O-tert-butyldimethylsilyl-17α-hydroxypropargyl-β-estradiolyl 2-phenylquinoline-4-carboxylate (959414-78-9)

Guidance literature:

With dmap; N,N'-1,2-ethylenediylbis-(L-cysteine) diethyl ester dihydrochloride; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1039/b708947c

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 3-O-tert-butyldimethylsilyl-17α-hydroxypropargyl-β-estradiolyl 2-phenylquinoline-4-carboxylate (959414-78-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0 - 25 °C

2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C

2.2: 17 h / 25 °C

3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 20 °C

With 2,6-dimethylpyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c1ob05629h

Reference yield:

ethinyl estradiol (57-63-6) → 3-O-tert-butyldimethylsilyl-17α-hydroxypropargyl-β-estradiolyl 2-phenylquinoline-4-carboxylate (959414-78-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0 - 25 °C

2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C

2.2: 17 h / 25 °C

3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 20 °C

With 2,6-dimethylpyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c1ob05629h

upstream raw materials:

cinchophen

3-(tert-butyldimethylsilyloxy)-17α-(3'-hydroxyprop-1'-ynyl)estradiol

t-butyldimethylsiyl triflate

ethinyl estradiol

Downstream raw materials:

17α-hydroxypropargyl-β-estradiolyl 2-phenylquinoline-4-carboxylate