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

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 hydrogen glutarate
CAS No.:502687-91-4
Molecular Formula:C₄₄H₇₈O₇Si₂
Molecular Weight:775.27
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 hydrogen glutarate

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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 hydrogen glutarate

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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 hydrogen glutarate

There total 10 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 hydrogen glutarate 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: 77.0%

: 108-55-4
glutaric anhydride,

: 502687-90-3
(5Z,7E)-(1R,3S,20S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-trien-16α,25-diol

: 502687-91-4
(5Z,7E)-(1R,3S,20S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-trien-25-ol-16α-yl hydrogen glutarate

Guidance literature:: With dmap; In dichloromethane; at 4 ℃; for 72h;
DOI:10.1021/jo026061s

Reference yield:

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

: 502687-91-4
(5Z,7E)-(1R,3S,20S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-trien-25-ol-16α-yl hydrogen glutarate

Guidance literature:: Multi-step reaction with 9 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

8.1: 100 percent / KOH / methanol / 6 h / 40 °C

9.1: 77 percent / DMAP / CH₂Cl₂ / 72 h / 4 °C

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

Reference yield:

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

: 502687-91-4
(5Z,7E)-(1R,3S,20S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-trien-25-ol-16α-yl hydrogen glutarate

Guidance literature:: Multi-step reaction with 4 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

3.1: 100 percent / KOH / methanol / 6 h / 40 °C

4.1: 77 percent / DMAP / CH₂Cl₂ / 72 h / 4 °C

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