Technology Process of (1S,3R,5Z,7E,20S)-1,3-di-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]-17α,21-cyclo-9,10-secocholesta-5,7,10(19)-trien-22-yne
There total 11 articles about (1S,3R,5Z,7E,20S)-1,3-di-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]-17α,21-cyclo-9,10-secocholesta-5,7,10(19)-trien-22-yne which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide;
With
n-butyllithium;
In
tetrahydrofuran; hexane;
at -78 ℃;
for 1h;
(8β,20S)-25-[(methoxymethyl)oxy]-des-A,B-17α,21-cyclocholest-22-yn-8-one;
In
tetrahydrofuran; hexane;
at -78 - -40 ℃;
for 5h;
Further stages.;
DOI:10.1021/jo0625195
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 94 percent / pyridine; Zn; PPh3 / CH2Cl2 / 5 h
2.1: 85 percent / BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
3.1: 88 percent / n-BuLi; BF3*OEt2 / hexane; tetrahydrofuran / 6 h / 20 °C
4.1: 92 percent / iPr2NEt / CH2Cl2 / 24 h / 0 °C
5.1: 96 percent / n-Bu4NF / tetrahydrofuran / 12 h / Heating
6.1: 90 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 8 h / 20 °C
7.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
7.2: 92 percent / tetrahydrofuran; hexane / 5 h / -78 - -40 °C
With
pyridine; dipyridinium dichromate; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc;
In
tetrahydrofuran; hexane; dichloromethane;
7.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0625195
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 85 percent / BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.1: 88 percent / n-BuLi; BF3*OEt2 / hexane; tetrahydrofuran / 6 h / 20 °C
3.1: 92 percent / iPr2NEt / CH2Cl2 / 24 h / 0 °C
4.1: 96 percent / n-Bu4NF / tetrahydrofuran / 12 h / Heating
5.1: 90 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 8 h / 20 °C
6.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
6.2: 92 percent / tetrahydrofuran; hexane / 5 h / -78 - -40 °C
With
dipyridinium dichromate; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; hexane; dichloromethane;
6.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0625195
![(8β,20S)-25-[(methoxymethyl)oxy]-des-A,B-17α,21-cyclocholest-22-yn-8-one](/Databaselist/images/loading.webp)
