(5Z,7E)-(1S,3R)-1,3-bis[(t-butyldimethyl-silyl)oxy]-24-phenylsulfonyl-22,23-dinor-9,10-secochola-5,7,10⁽¹⁹⁾-triene

Base Information

• Chemical Name: (5Z,7E)-(1S,3R)-1,3-bis[(t-butyldimethyl-silyl)oxy]-24-phenylsulfonyl-22,23-dinor-9,10-secochola-5,7,10⁽¹⁹⁾-triene
• CAS No.: 223538-02-1
• Molecular Formula: C₄₀H₆₆O₄SSi₂
• Molecular Weight: 699.199

Synonyms:(5Z,7E)-(1S,3R)-1,3-bis[(t-butyldimethyl-silyl)oxy]-24-phenylsulfonyl-22,23-dinor-9,10-secochola-5,7,10⁽¹⁹⁾-triene

Chemical Property of (5Z,7E)-(1S,3R)-1,3-bis[(t-butyldimethyl-silyl)oxy]-24-phenylsulfonyl-22,23-dinor-9,10-secochola-5,7,10⁽¹⁹⁾-triene

Chemical Property:

Purity/Quality:

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Technology Process of (5Z,7E)-(1S,3R)-1,3-bis[(t-butyldimethyl-silyl)oxy]-24-phenylsulfonyl-22,23-dinor-9,10-secochola-5,7,10⁽¹⁹⁾-triene

There total 7 articles about (5Z,7E)-(1S,3R)-1,3-bis[(t-butyldimethyl-silyl)oxy]-24-phenylsulfonyl-22,23-dinor-9,10-secochola-5,7,10⁽¹⁹⁾-triene 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: 88.0%

sodium phenylsulfonate (515-42-4) + (5Z,7E)-(1S,3R,20S)-1,3-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-22,23-dinor-5,7,10(19)-cholatrienol 22-p-toluenesulfonate (114694-13-2) → (5Z,7E)-(1S,3R)-1,3-bis[(t-butyldimethyl-silyl)oxy]-24-phenylsulfonyl-22,23-dinor-9,10-secochola-5,7,10(19)-triene (223538-02-1)

Guidance literature:

(5Z,7E)-(1S,3R,20S)-1,3-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-22,23-dinor-5,7,10(19)-cholatrienol 22-p-toluenesulfonate; With lithium carbonate; lithium bromide; In N,N-dimethyl-formamide; at 80 ℃; for 0.333333h;

sodium phenylsulfonate; In N,N-dimethyl-formamide; at 80 ℃; for 2.5h;

DOI:10.1016/S0039-128X(02)00038-7

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (5Z,7E)-(1S,3R)-1,3-bis[(t-butyldimethyl-silyl)oxy]-24-phenylsulfonyl-22,23-dinor-9,10-secochola-5,7,10(19)-triene (223538-02-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 98 percent / imidazole / dimethylformamide / 24 h / 20 °C

2.1: 97 percent / sodium borohydride / CH₂Cl₂; methanol / 0.25 h / 20 °C

3.1: 60 percent / KOH / methanol / 48 h / 95 °C

4.1: 90 percent / triethylamine; 4,4-dimethylaminopyridine / CH₂Cl₂ / 28 h / 20 °C

5.1: lithium bromide dihydrate; lithium carbonate / dimethylformamide / 0.33 h / 80 °C

5.2: 88 percent / dimethylformamide / 2.5 h / 80 °C

With 1H-imidazole; dmap; potassium hydroxide; sodium tetrahydroborate; lithium carbonate; triethylamine; lithium bromide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0039-128X(02)00038-7

Reference yield:

(5Z,7E)-(1S,3R,20S)-1,3-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-22,23-dinor-5,7,10(19)-cholatrien-24-ol (114694-12-1) → (5Z,7E)-(1S,3R)-1,3-bis[(t-butyldimethyl-silyl)oxy]-24-phenylsulfonyl-22,23-dinor-9,10-secochola-5,7,10(19)-triene (223538-02-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / triethylamine; 4,4-dimethylaminopyridine / CH₂Cl₂ / 28 h / 20 °C

2.1: lithium bromide dihydrate; lithium carbonate / dimethylformamide / 0.33 h / 80 °C

2.2: 88 percent / dimethylformamide / 2.5 h / 80 °C

With dmap; lithium carbonate; triethylamine; lithium bromide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0039-128X(02)00038-7

upstream raw materials:

sodium phenylsulfonate

(5Z,7E)-(1S,3R,20S)-1,3-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-22,23-dinor-5,7,10(19)-cholatrienol 22-p-toluenesulfonate

tert-butyldimethylsilyl chloride

(5Z,7E)-(1S,3R,20S)-1,3-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-22,23-dinor-5,7,10(19)-cholatrien-24-ol

Downstream raw materials:

ethyl (5Z,7E,23aE)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-23-hydroxy-23a-methyl-23a,23b-dihomo-9,10-secochola-5,7,10⁽¹⁹⁾,23-tetraene-24-oate

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

(4E,6E)-(R)-8-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-3-ethyl-5-methyl-nona-4,6-dien-3-ol

(5E,7E)-(R)-9-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-6-methyl-4-propyl-deca-5,7-dien-4-ol

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