Technology Process of methyl 2β-<(E)-3-hydroxy-1-methylprop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate
There total 21 articles about methyl 2β-<(E)-3-hydroxy-1-methylprop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 1.) O3, 2.) Me2S / 1.) MeOH, -78 deg C, 30 min, 2.) MeOH, RT
2: 1.) 4 Angstroem molecular sieves, 3.) NaBH4
3: 1.) O3, 2.) Ph3P / 1.) MeOH, -78 deg C, 2.) MeOH, RT, 2 h
4: 88 percent / toluene; CH2Cl2 / 12 h / 45 °C
5: 95 percent / DMAP, Et3N / CH2Cl2 / 16 h
6: 98 percent / aq. AcOH / methanol / 25 h / 95 °C
7: NaIO4 / tetrahydrofuran; H2O / 4 h / 25 °C
8: CrCl2 / tetrahydrofuran / 3 h / 0 °C
9: 76 percent / 10percent TlOH, Pd(PPh3)4 / methanol; tetrahydrofuran / 0.07 h / 25 °C
10: 64 percent / BHT / toluene / 16 h / 150 °C
11: K2CO3 / methanol / Ambient temperature
With
chromium dichloride; dmap; sodium tetrahydroborate; sodium periodate; tetrakis(triphenylphosphine) palladium(0); TlOH; dimethylsulfide; 2,6-di-tert-butyl-4-methyl-phenol; 4 A molecular sieve; potassium carbonate; ozone; acetic acid; triethylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1021/ja00059a024
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 1.) 4 Angstroem molecular sieves, 3.) NaBH4
2: 1.) O3, 2.) Ph3P / 1.) MeOH, -78 deg C, 2.) MeOH, RT, 2 h
3: 88 percent / toluene; CH2Cl2 / 12 h / 45 °C
4: 95 percent / DMAP, Et3N / CH2Cl2 / 16 h
5: 98 percent / aq. AcOH / methanol / 25 h / 95 °C
6: NaIO4 / tetrahydrofuran; H2O / 4 h / 25 °C
7: CrCl2 / tetrahydrofuran / 3 h / 0 °C
8: 76 percent / 10percent TlOH, Pd(PPh3)4 / methanol; tetrahydrofuran / 0.07 h / 25 °C
9: 64 percent / BHT / toluene / 16 h / 150 °C
10: K2CO3 / methanol / Ambient temperature
With
chromium dichloride; dmap; sodium tetrahydroborate; sodium periodate; tetrakis(triphenylphosphine) palladium(0); TlOH; 2,6-di-tert-butyl-4-methyl-phenol; 4 A molecular sieve; potassium carbonate; ozone; acetic acid; triethylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1021/ja00059a024
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 88 percent / toluene; CH2Cl2 / 12 h / 45 °C
2: 95 percent / DMAP, Et3N / CH2Cl2 / 16 h
3: 98 percent / aq. AcOH / methanol / 25 h / 95 °C
4: NaIO4 / tetrahydrofuran; H2O / 4 h / 25 °C
5: CrCl2 / tetrahydrofuran / 3 h / 0 °C
6: 76 percent / 10percent TlOH, Pd(PPh3)4 / methanol; tetrahydrofuran / 0.07 h / 25 °C
7: 64 percent / BHT / toluene / 16 h / 150 °C
8: K2CO3 / methanol / Ambient temperature
With
chromium dichloride; dmap; sodium periodate; tetrakis(triphenylphosphine) palladium(0); TlOH; 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate; acetic acid; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1021/ja00059a024
