Technology Process of (3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol
There total 10 articles about (3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
bimatoprost;
With
butylboronic acid;
In
dichloromethane;
for 0.666667h;
Reflux;
t-butyldimethylsiyl triflate;
With
2,6-dimethylpyridine;
In
dichloromethane;
at 20 ℃;
Cooling with ice;
- Guidance literature:
-
(5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide;
With
valerianate de potassium;
In
tetrahydrofuran;
at 0 ℃;
for 0.5h;
Inert atmosphere;
Schlenk technique;
(3aR,4R,5R,6aS)-4-[3S-(t-butyldimethylsiloxy)-5-phenyl-1E-pentenyl]-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-ol;
In
tetrahydrofuran;
at 0 - 20 ℃;
for 4h;
Inert atmosphere;
Schlenk technique;
DOI:10.1021/ol503520f
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: sodium hydride / toluene; mineral oil / 20 h / Reflux
2.1: Schwartz's reagent / dichloromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique
2.2: 1 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
3.1: tert.-butyl lithium / diethyl ether; pentane / 4 h / -78 - -40 °C / Inert atmosphere; Schlenk technique
3.2: 0.5 h / -30 °C / Inert atmosphere; Schlenk technique
4.1: ozone / methanol; dichloromethane / -78 °C
4.2: -78 - 20 °C
5.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C
6.1: valerianate de potassium / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique
6.2: 4 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
With
Schwartz's reagent; tert.-butyl lithium; valerianate de potassium; sodium hydride; diisobutylaluminium hydride; ozone;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; mineral oil; pentane;
DOI:10.1021/ol503520f
