Technology Process of 6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-2(S),6(R)-dimethyl-5(R)-(phenethyloxy)-1,2,3,4,4a(R),5,6,7,8,8a(R)-decahydronaphthyl-1(S)>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one
There total 10 articles about 6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-2(S),6(R)-dimethyl-5(R)-(phenethyloxy)-1,2,3,4,4a(R),5,6,7,8,8a(R)-decahydronaphthyl-1(S)>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one which
guide to synthetic route it.
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synthetic route:
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127343-21-9
6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-2(S),6(R)-dimethyl-5(R)-(phenethyloxy)-1,2,3,4,4a(R),5,6,7,8,8a(R)-decahydronaphthyl-1(S)>ethyl>-4(R)-<(tert-butyldiphenylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one
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127343-09-3
6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-2(S),6(R)-dimethyl-5(R)-(phenethyloxy)-1,2,3,4,4a(R),5,6,7,8,8a(R)-decahydronaphthyl-1(S)>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one
- Guidance literature:
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With
tetrabutyl ammonium fluoride; acetic acid;
In
tetrahydrofuran;
at 45 ℃;
for 2h;
DOI:10.1021/jm00112a027
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127343-09-3
6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-2(S),6(R)-dimethyl-5(R)-(phenethyloxy)-1,2,3,4,4a(R),5,6,7,8,8a(R)-decahydronaphthyl-1(S)>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one
- Guidance literature:
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Multi-step reaction with 3 steps
1: (+/-)-camphorsulfonic acid / CH2Cl2 / 3 h
2: H2 / 10percent Pd/C / ethyl acetate / 8 h / 25 °C / 760 Torr
3: 100 percent / tetra-butylammonium fluoride, AcOH / tetrahydrofuran / 2 h / 45 °C
With
camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; acetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1021/jm00112a027
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127343-09-3
6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-2(S),6(R)-dimethyl-5(R)-(phenethyloxy)-1,2,3,4,4a(R),5,6,7,8,8a(R)-decahydronaphthyl-1(S)>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one
- Guidance literature:
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Multi-step reaction with 9 steps
1: 1.) H2, 2.) thiourea / 1.) (Ph3P)3RhCl / 1.) toluene, ethanol, 60 psi, RT, 40 h, 2.) toluene, 60 deg C, 1.5
2: imidazole / dimethylformamide / 4 h / 25 °C
3: N-bromosuccinimide, H2O / tetrahydrofuran; dimethylsulfoxide / 1 h / 5 °C
4: pyridinium chlorochromate (PCC), 4 A sieves / CH2Cl2 / 1 h / 0 - 20 °C
5: Zn, acetic acid / tetrahydrofuran / 1 h / Ambient temperature
6: NaBH4 / tetrahydrofuran; H2O / 0.58 h / 0 °C
7: (+/-)-camphorsulfonic acid / CH2Cl2 / 3 h
8: H2 / 10percent Pd/C / ethyl acetate / 8 h / 25 °C / 760 Torr
9: 100 percent / tetra-butylammonium fluoride, AcOH / tetrahydrofuran / 2 h / 45 °C
With
1H-imidazole; sodium tetrahydroborate; N-Bromosuccinimide; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; hydrogen; acetic acid; thiourea; pyridinium chlorochromate; zinc;
palladium on activated charcoal; Wilkinson's catalyst;
In
tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm00112a027