(5Z,7E,24E)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-24-methyl-24a,26,27-trihomo-9,10-secocholesta-5,7,10⁽¹⁹⁾,24-tetraen-23,25-diol

Base Information

• Chemical Name: (5Z,7E,24E)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-24-methyl-24a,26,27-trihomo-9,10-secocholesta-5,7,10⁽¹⁹⁾,24-tetraen-23,25-diol
• CAS No.: 501431-53-4
• Molecular Formula: C₄₉H₈₂O₆SSi₂
• Molecular Weight: 855.423

Synonyms:(5Z,7E,24E)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-24-methyl-24a,26,27-trihomo-9,10-secocholesta-5,7,10⁽¹⁹⁾,24-tetraen-23,25-diol

Chemical Property of (5Z,7E,24E)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-24-methyl-24a,26,27-trihomo-9,10-secocholesta-5,7,10⁽¹⁹⁾,24-tetraen-23,25-diol

Chemical Property:

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Technology Process of (5Z,7E,24E)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-24-methyl-24a,26,27-trihomo-9,10-secocholesta-5,7,10⁽¹⁹⁾,24-tetraen-23,25-diol

There total 10 articles about (5Z,7E,24E)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-24-methyl-24a,26,27-trihomo-9,10-secocholesta-5,7,10⁽¹⁹⁾,24-tetraen-23,25-diol 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: 32.0%

ethylmagnesium bromide (925-90-6) + 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) → (5Z,7E,24E)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-24-methyl-24a,26,27-trihomo-9,10-secocholesta-5,7,10(19),24-tetraen-23,25-diol (501431-53-4)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 20 ℃; for 2h;

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

Reference yield:

ethyl (E)-3-formyl-2-butenoate (62054-49-3) → (5Z,7E,24E)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-24-methyl-24a,26,27-trihomo-9,10-secocholesta-5,7,10(19),24-tetraen-23,25-diol (501431-53-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / n-BuLi / tetrahydrofuran / 0.25 h / -70 °C

2: 32 percent / diethyl ether; tetrahydrofuran / 2 h / 20 °C

With n-butyllithium; In tetrahydrofuran; diethyl ether;

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

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (5Z,7E,24E)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-24-methyl-24a,26,27-trihomo-9,10-secocholesta-5,7,10(19),24-tetraen-23,25-diol (501431-53-4)

Guidance literature:

Multi-step reaction with 7 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

7.1: 32 percent / diethyl ether; tetrahydrofuran / 2 h / 20 °C

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

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

upstream raw materials:

ethylmagnesium bromide

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

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

tert-butyldimethylsilyl chloride

Downstream raw materials:

(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

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