(5Z,7E,20R,23S)-24,24-difluoro-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-23-hydroxy-24-ethoxycarbonyl-9,10-seco-5,7,10(19)-cholatriene

Base Information

• Chemical Name: (5Z,7E,20R,23S)-24,24-difluoro-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-23-hydroxy-24-ethoxycarbonyl-9,10-seco-5,7,10(19)-cholatriene
• CAS No.: 183274-06-8
• Molecular Formula: C₃₉H₆₈F₂O₅Si₂
• Molecular Weight: 711.134
• Mol file: 183274-06-8.mol

Synonyms:

Chemical Property of (5Z,7E,20R,23S)-24,24-difluoro-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-23-hydroxy-24-ethoxycarbonyl-9,10-seco-5,7,10(19)-cholatriene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5Z,7E,20R,23S)-24,24-difluoro-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-23-hydroxy-24-ethoxycarbonyl-9,10-seco-5,7,10(19)-cholatriene

There total 1 articles about (5Z,7E,20R,23S)-24,24-difluoro-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-23-hydroxy-24-ethoxycarbonyl-9,10-seco-5,7,10(19)-cholatriene 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:

Ethyl bromodifluoroacetate (667-27-6) + (5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene (143884-26-8) → (5Z,7E,20R,23S)-24,24-difluoro-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-23-hydroxy-24-ethoxycarbonyl-9,10-seco-5,7,10(19)-cholatriene (183274-06-8) + (5Z,7E,20R,23R)-24,24-difluoro-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-23-hydroxy-24-ethoxycarbonyl-9,10-seco-5,7,10(19)-cholatriene (183274-05-7)

Guidance literature:

With zinc; Yield given; Multistep reaction. Yields of byproduct given; 1.) THF, reflux, 2 min, 2.) THF, reflux, 2 min;

DOI:10.1248/cpb.46.1932

Reference yield: 48.0%

(R)-methoxytrifluoromethylphenylacetyl chloride (20445-33-4,39637-99-5) + (5Z,7E,20R,23S)-24,24-difluoro-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-23-hydroxy-24-ethoxycarbonyl-9,10-seco-5,7,10(19)-cholatriene (183274-06-8) → 5-(4-{2-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene}-7a-methyl-octahydro-inden-1-yl)-2,2-difluoro-3-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-hexanoic acid ethyl ester

Guidance literature:

With dmap; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1248/cpb.46.1932

Reference yield: 38.0%

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4) + (5Z,7E,20R,23S)-24,24-difluoro-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-23-hydroxy-24-ethoxycarbonyl-9,10-seco-5,7,10(19)-cholatriene (183274-06-8) → 5-(4-{2-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene}-7a-methyl-octahydro-inden-1-yl)-2,2-difluoro-3-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-hexanoic acid ethyl ester

Guidance literature:

With dmap; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1248/cpb.46.1932

upstream raw materials:

Ethyl bromodifluoroacetate

(5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene

Downstream raw materials:

(23S)-24,24-difluoro-1α,23,25-dihydroxyvitamin D₃