(5Z,7E)-(1R,3S,20S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-trien-25-ol-16α-yl acetate

Base Information

Chemical Name:(5Z,7E)-(1R,3S,20S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-trien-25-ol-16α-yl acetate
CAS No.:502687-89-0
Molecular Formula:C₄₁H₇₄O₅Si₂
Molecular Weight:703.207
Hs Code.:

Synonyms:(5Z,7E)-(1R,3S,20S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-trien-25-ol-16α-yl acetate

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Chemical Property of (5Z,7E)-(1R,3S,20S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-trien-25-ol-16α-yl acetate

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Technology Process of (5Z,7E)-(1R,3S,20S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-trien-25-ol-16α-yl acetate

There total 8 articles about (5Z,7E)-(1R,3S,20S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-trien-25-ol-16α-yl acetate 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: 61.0%

: 81522-68-1
[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

: 502687-88-9
(20S)-des-A,B-25-[(trimethylsilyl)oxy]cholestan-8-on-16α-yl acetate

: 502687-89-0
(5Z,7E)-(1R,3S,20S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-trien-25-ol-16α-yl acetate

: Acetic acid (1R,2R,3aS,7aS)-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((S)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-7a-methyl-octahydro-inden-2-yl ester

Guidance literature:: [(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.416667h;

(20S)-des-A,B-25-[(trimethylsilyl)oxy]cholestan-8-on-16α-yl acetate; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;
DOI:10.1021/jo026061s

Reference yield:

: 67883-17-4
1-bromo-3-methyl-3-trimethyl-silyloxybutane

: 502687-89-0
(5Z,7E)-(1R,3S,20S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-trien-25-ol-16α-yl acetate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 90 percent / Mg; Li₂CuCl₄ / tetrahydrofuran / 1 h / 0 °C

2.1: BH₃*THF / tetrahydrofuran; hexane / 0 °C

2.2: 64 percent / 30percent H₂O₂; aq. NaOH / tetrahydrofuran / 2 h / 0 °C

3.1: 100 percent / pyridine / 3 h / 20 °C

4.1: 79 percent / 40percent aq. HF / acetonitrile / 8 h / 20 °C

5.1: 95 percent / PDC / CH₂Cl₂ / 6 h / 20 °C

6.1: 90 percent / DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

7.1: n-BuLi / tetrahydrofuran / 0.42 h / -78 °C

7.2: 61 percent / tetrahydrofuran / -78 - 20 °C

With dmap; dipyridinium dichromate; n-butyllithium; borane-THF; dilithium tetrachlorocuprate; magnesium; triethylamine; In tetrahydrofuran; pyridine; hexane; dichloromethane; acetonitrile;
DOI:10.1021/jo026061s

Reference yield:

: 502687-96-9
(20S)-des-A,B-25-hydroxycholestan-8-on-16α-yl acetate

: 502687-89-0
(5Z,7E)-(1R,3S,20S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-trien-25-ol-16α-yl acetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 90 percent / DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

2.1: n-BuLi / tetrahydrofuran / 0.42 h / -78 °C

2.2: 61 percent / tetrahydrofuran / -78 - 20 °C

With dmap; n-butyllithium; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo026061s