Technology Process of (3S,4S,5S,6S)-4-Benzyloxy-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,5-dimethyl-tetrahydro-pyran-2-one
There total 11 articles about (3S,4S,5S,6S)-4-Benzyloxy-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,5-dimethyl-tetrahydro-pyran-2-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
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Multi-step reaction with 11 steps
1.1: (+)-diisopinocampheylborane / 24 h / -23 °C
1.2: 96 percent / NaOH; H2O2 / H2O / 6 h / 20 °C
2.1: PCC / CH2Cl2 / 3 h / 20 °C
3.1: m-CPBA; NaHCO3 / CH2Cl2 / 10 h / 20 °C
4.1: 88 percent / LiAlH4 / tetrahydrofuran / 4 h / 0 - 20 °C
5.1: 83 percent / imidazole / CH2Cl2 / 2 h / 0 - 20 °C
6.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C
7.1: NaBH4 / methanol; tetrahydrofuran / 1 h / 0 - 20 °C
8.1: 88 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C
9.1: 71 percent / IBX / dimethylsulfoxide; CH2Cl2 / 6 h / 20 °C
10.1: NaCNBH3 / methanol; acetic acid / 1 h / 20 °C / pH 5.5
11.1: imidazole / CH2Cl2 / 1.5 h / 0 - 20 °C
With
1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; diisopinocampheylborane; tetrabutyl ammonium fluoride; sodium cyanoborohydride; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; dichloromethane; acetic acid; dimethyl sulfoxide;
3.1: Baeyer-Villiger oxidation;
DOI:10.1016/S0040-4039(01)00799-7
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 88 percent / LiAlH4 / tetrahydrofuran / 4 h / 0 - 20 °C
2: 83 percent / imidazole / CH2Cl2 / 2 h / 0 - 20 °C
3: 95 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C
4: NaBH4 / methanol; tetrahydrofuran / 1 h / 0 - 20 °C
5: 88 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C
6: 71 percent / IBX / dimethylsulfoxide; CH2Cl2 / 6 h / 20 °C
7: NaCNBH3 / methanol; acetic acid / 1 h / 20 °C / pH 5.5
8: imidazole / CH2Cl2 / 1.5 h / 0 - 20 °C
With
1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sodium cyanoborohydride; Dess-Martin periodane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; dichloromethane; acetic acid; dimethyl sulfoxide;
DOI:10.1016/S0040-4039(01)00799-7
