Technology Process of (5Z,7E,22E)-(1S,3R,24R)-25-(5-butyloxazole-2-yl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
There total 14 articles about (5Z,7E,22E)-(1S,3R,24R)-25-(5-butyloxazole-2-yl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol 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:
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(5Z,7E,22E)-(1S,3R,24R)-1,3-bis(tert-butyldimethylsilyloxy)-24-hydroxy-25-(5-butyloxazol-2-yl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene
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198760-31-5
(5Z,7E,22E)-(1S,3R,24R)-25-(5-butyloxazole-2-yl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
- Guidance literature:
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With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
at 20 - 22 ℃;
for 7h;
DOI:10.1021/op060130d
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198760-31-5
(5Z,7E,22E)-(1S,3R,24R)-25-(5-butyloxazole-2-yl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
- Guidance literature:
-
-
-
198760-31-5
(5Z,7E,22E)-(1S,3R,24R)-25-(5-butyloxazole-2-yl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
- Guidance literature:
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Multi-step reaction with 9 steps
1.1: sodium hydroxide / water / 2 h / 40 °C
2.1: diisopropyl-carbodiimide / dichloromethane / 4 h / -10 - 20 °C
3.1: tetrahydrofuran / 24 h / 15 - 22 °C
4.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1.17 h / -40 °C
5.1: sulfuric acid / dichloromethane / 14 h / 20 - 40 °C
6.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -50 °C / Inert atmosphere
6.2: 2 h / -50 - 0 °C / Inert atmosphere
7.1: sodium hydride / tetrahydrofuran; paraffin oil / 1 h / 0 - 20 °C
7.2: 20 h / 20 - 50 °C
8.1: anthracene; triethylamine / dichloromethane / 0.5 h / 10 °C / Inert atmosphere; UV-irradiation
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 - 22 °C
With
n-butyllithium; oxalyl dichloride; anthracene; sulfuric acid; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; sodium hydroxide; diisopropyl-carbodiimide;
In
tetrahydrofuran; hexane; dichloromethane; water; paraffin oil;
4.1: |Swern Oxidation / 4.2: |Swern Oxidation / 6.1: |Claisen Condensation / 7.1: |Wittig-Horner Reaction / 7.2: |Wittig-Horner Reaction;
DOI:10.1021/op060130d