Technology Process of (2R,3R)-5-[N-(tert-butoxycarbonyl)amino]-1-(tert-butyl-dimethylsilyloxy)pentan-2,3-diol
There total 1 articles about (2R,3R)-5-[N-(tert-butoxycarbonyl)amino]-1-(tert-butyl-dimethylsilyloxy)pentan-2,3-diol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: dimethylsulfoxide; oxalyl chloride; triethylamine / CH2Cl2 / -78 - 20 °C
2.1: NaH / tetrahydrofuran / 0.17 h / 0 °C
2.2: 2.86 g / tetrahydrofuran / 1 h / -50 - 20 °C
3.1: 99 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 °C
4.1: 89 percent / imidazole / dimethylformamide / 3 h / 20 °C
5.1: AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 20 h / 0 °C
With
1H-imidazole; oxalyl dichloride; methanesulfonamide; AD-mix-β; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
1.1: Swern oxidation / 2.2: Horner-Wittig reaction / 5.1: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetasy.2007.03.022
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: NaH / tetrahydrofuran / 1.5 h / 0 °C
1.2: tetrabutylammonium iodide / tetrahydrofuran / 4 h / 20 °C
2.1: p-TsOH / methanol / 3 h / 20 °C
3.1: IBX / tetrahydrofuran; dimethylsulfoxide / 4 h / 20 °C
4.1: NaH / tetrahydrofuran / 0.17 h / 0 °C
4.2: 2.86 g / tetrahydrofuran / 0.5 h / Heating
5.1: DIBAL-H / tetrahydrofuran / 5 h / 20 °C
6.1: PdCl2(MeCN)2 / tetrahydrofuran / 3 h / 20 °C
7.1: O3 / CH2Cl2; methanol / -78 °C
7.2: NaBH4 / CH2Cl2; methanol / -78 - 20 °C
8.1: aq. HCl / methanol / 5 h / 70 °C
9.1: H2 / Pd/C / acetic acid / 48 h / 20 °C
With
hydrogenchloride; hydrogen; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
dichloro bis(acetonitrile) palladium(II); palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; acetic acid; dimethyl sulfoxide;
4.2: Horner-Wittig reaction;
DOI:10.1016/j.tetasy.2007.03.022
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: NaH / tetrahydrofuran / 1.5 h / 0 °C
1.2: tetrabutylammonium iodide / tetrahydrofuran / 4 h / 20 °C
2.1: p-TsOH / methanol / 3 h / 20 °C
3.1: IBX / tetrahydrofuran; dimethylsulfoxide / 4 h / 20 °C
4.1: NaH / tetrahydrofuran / 0.17 h / 0 °C
4.2: 2.86 g / tetrahydrofuran / 0.5 h / Heating
5.1: DIBAL-H / tetrahydrofuran / 5 h / 20 °C
6.1: PdCl2(MeCN)2 / tetrahydrofuran / 3 h / 20 °C
With
sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
dichloro bis(acetonitrile) palladium(II);
In
tetrahydrofuran; methanol; dimethyl sulfoxide;
4.2: Horner-Wittig reaction;
DOI:10.1016/j.tetasy.2007.03.022
