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

Base Information

• Chemical Name: 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
• CAS No.: 501431-51-2
• Molecular Formula: C₄₇H₇₆O₇SSi₂
• Molecular Weight: 841.353

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 8 articles about 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 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%

ethyl (E)-3-formyl-2-butenoate (62054-49-3) + (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) → 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 (501431-51-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -70 ℃; for 0.25h;

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

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 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 (501431-51-2)

Guidance literature:

Multi-step reaction with 6 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

6.1: 88 percent / n-BuLi / tetrahydrofuran / 0.25 h / -70 °C

With 1H-imidazole; dmap; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; lithium carbonate; triethylamine; lithium bromide; In tetrahydrofuran; 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)-cholatrienol 22-p-toluenesulfonate (114694-13-2) → 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 (501431-51-2)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 88 percent / dimethylformamide / 2.5 h / 80 °C

2.1: 88 percent / n-BuLi / tetrahydrofuran / 0.25 h / -70 °C

With n-butyllithium; lithium carbonate; lithium bromide; In tetrahydrofuran; N,N-dimethyl-formamide;

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

upstream raw materials:

ethyl (E)-3-formyl-2-butenoate

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

tert-butyldimethylsilyl chloride

(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

Downstream raw materials:

(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

(6E,8E)-(R)-10-{(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}-5-butyl-7-methyl-undeca-6,8-dien-5-ol

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