Technology Process of (2R,3R,4S)-5-[(tert-butyldiphenylsilyl)oxy]-2-hydroxy-3-methyl-4-pentanolide
There total 15 articles about (2R,3R,4S)-5-[(tert-butyldiphenylsilyl)oxy]-2-hydroxy-3-methyl-4-pentanolide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH2Cl2 / 3.5 h / Ambient temperature
2: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane
3: 30percent H2O2 / 0 °C
4: 98 percent / diethyl ether / 15 h
5: 92 percent / CaCO3 / toluene / 3 h / Heating
6: hydrogen / 5percent Rh/Al2O3 / ethyl acetate / 1 h / 2585.7 Torr
7: 1.) potassium hexamethyldisilazide 2.) oxodiperoxomolybdenum-pyridine-HMPA-complex / 1.) THF, toluene, -78 deg C, 20 min; 2.) THF, toluene, -55 deg C, 40 min.
With
dmap; MoO5*pyridine*HMPA; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; triethylamine; calcium carbonate; lithium hexamethyldisilazane;
Rh/Al2O3;
In
diethyl ether; dichloromethane; ethyl acetate; toluene;
DOI:10.1016/S0040-4020(01)87683-3
- Guidance literature:
-
Multi-step reaction with 2 steps
1: H2 / Rh-Al2O3 / ethyl acetate / 1 h / Ambient temperature
2: 77 percent / potassium hexamethyldisilazide, oxodiperoxymolybdenum-pyridine-HMPA complex / tetrahydrofuran / 1.5 h / -78 - -30 °C
With
MoO5*pyridine*HMPA; hydrogen; potassium hexamethylsilazane;
rhodium on alumina;
In
tetrahydrofuran; ethyl acetate;
DOI:10.1016/S0040-4020(97)00624-8
- Guidance literature:
-
Multi-step reaction with 4 steps
1: 100 percent / diethyl ether / 24 h / Ambient temperature
2: 92 percent / CaCO3 / toluene / 3 h / Heating
3: 100 percent / H2 / 10percent Pd/Al2O3 / ethyl acetate / 1 h / 2585.7 Torr / Ambient temperature
4: 1.) LiHMDS, 2.) MoOPH / 1.) THF, -78 deg C, 0.5 h, 2.) THF, -50 deg C, 1 h
With
MoO5*pyridine*HMPA; hydrogen; calcium carbonate; lithium hexamethyldisilazane;
palladium/alumina;
In
diethyl ether; ethyl acetate; toluene;
DOI:10.1021/jo00382a043
