Technology Process of 4-{(4S,5R)-5-[(1E,3E,5E,7E)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-1,3,5,7-tetraenyl]-2-oxo-[1,3]dioxolan-4-yl}-butyric acid ethyl ester
There total 22 articles about 4-{(4S,5R)-5-[(1E,3E,5E,7E)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-1,3,5,7-tetraenyl]-2-oxo-[1,3]dioxolan-4-yl}-butyric acid ethyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 95 percent / H2 / 10percent Pd/C / ethanol
2: aq. TFA
3: p-TsOH / toluene
4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) THF, -35 deg C, 1 h, 2.) -70 to -10 deg C, 1 h
5: Et3N / tetrahydrofuran / 8 h / 0 °C
6: LHMDS / 1.) THF, -100 deg C, 5 min, 2.) HMPA, -100 deg C, 5 min; -50 deg C, 1 h
With
oxalyl dichloride; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; toluene;
DOI:10.1039/p19960001057
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 75 percent / BF3*OEt2 / diethyl ether / 1 h / -100 °C
2: 81 percent / pyridine / Ambient temperature
3: 95 percent / H2 / PtO2 / ethanol
4: aq.TFA / 1 h / 0 °C
5: PTSA / toluene / 6 h / Ambient temperature
7: 1) KHMDS / 1) THF, -105 deg C, 2) HMPA, -100 to -40 deg C
With
pyridine; boron trifluoride diethyl etherate; hydrogen; potassium hexamethylsilazane; toluene-4-sulfonic acid; trifluoroacetic acid;
platinum(IV) oxide;
In
diethyl ether; ethanol; toluene;
DOI:10.1016/S0040-4039(00)92034-3
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 81 percent / pyridine / Ambient temperature
2: 95 percent / H2 / PtO2 / ethanol
3: aq.TFA / 1 h / 0 °C
4: PTSA / toluene / 6 h / Ambient temperature
6: 1) KHMDS / 1) THF, -105 deg C, 2) HMPA, -100 to -40 deg C
With
pyridine; hydrogen; potassium hexamethylsilazane; toluene-4-sulfonic acid; trifluoroacetic acid;
platinum(IV) oxide;
In
ethanol; toluene;
DOI:10.1016/S0040-4039(00)92034-3