Technology Process of (4S,5R)-3-[(S)-3-{(4R,5R)-5-[(S)-5-(tert-butyldimethylsilyloxy)-4-methylpentyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}-2-hydroxypropanoyl]-4-methyl-5-phenyloxazolidin-2-one
There total 23 articles about (4S,5R)-3-[(S)-3-{(4R,5R)-5-[(S)-5-(tert-butyldimethylsilyloxy)-4-methylpentyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}-2-hydroxypropanoyl]-4-methyl-5-phenyloxazolidin-2-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: AD-Mix β; methanesulfonamide; water / 2-methyl-propan-2-ol / 14 h / 20 °C
1.2: 6.329 g / CSA / 14 h / 20 °C
2.1: 94 percent / DIBAL-H / tetrahydrofuran; hexane / 14 h / 20 °C
3.1: 97 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 4 h / 0 °C
4.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C
4.2: 87 percent / tetrahydrofuran / 0.5 h / 20 °C
5.1: 91 percent / hydrogen / Pd/Al2O3 / ethanol / 28 h / 20 °C / 2250.18 Torr
6.1: 88 percent / NaIO4 / RuCl3*H2O / CCl4; acetonitrile; H2O / 1.33 h / 20 °C
7.1: pivaloyl chloride; triethylamine / diethyl ether / 1 h / -30 °C
7.2: 80 percent / tetrahydrofuran; diethyl ether / 1 h / 0 °C
8.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C
8.2: 0.147 g / Davis' oxaziridine / tetrahydrofuran / 0.08 h / -84 °C
With
pyridine; sodium periodate; methanesulfonamide; water; hydrogen; sodium hexamethyldisilazane; pivaloyl chloride; diisobutylaluminium hydride; Dess-Martin periodane; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine;
ruthenium trichloride; palladium/alumina;
In
tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol;
4.2: Wittig olefination;
DOI:10.1002/ejoc.200600113
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 76 percent / 5 h / 90 °C
2.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C
2.2: 87 percent / tetrahydrofuran / 0.5 h / 20 °C
3.1: 91 percent / hydrogen / Pd/Al2O3 / ethanol / 28 h / 20 °C / 2250.18 Torr
4.1: 88 percent / NaIO4 / RuCl3*H2O / CCl4; acetonitrile; H2O / 1.33 h / 20 °C
5.1: pivaloyl chloride; triethylamine / diethyl ether / 1 h / -30 °C
5.2: 80 percent / tetrahydrofuran; diethyl ether / 1 h / 0 °C
6.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C
6.2: 0.147 g / Davis' oxaziridine / tetrahydrofuran / 0.08 h / -84 °C
With
sodium periodate; hydrogen; sodium hexamethyldisilazane; pivaloyl chloride; triethylamine;
ruthenium trichloride; palladium/alumina;
In
tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; water; acetonitrile;
2.2: Wittig olefination;
DOI:10.1002/ejoc.200600113
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 93 percent / iodine; imidazole; PPh3 / diethyl ether; acetonitrile / 0.5 h / 0 °C
2.1: 76 percent / 5 h / 90 °C
3.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C
3.2: 87 percent / tetrahydrofuran / 0.5 h / 20 °C
4.1: 91 percent / hydrogen / Pd/Al2O3 / ethanol / 28 h / 20 °C / 2250.18 Torr
5.1: 88 percent / NaIO4 / RuCl3*H2O / CCl4; acetonitrile; H2O / 1.33 h / 20 °C
6.1: pivaloyl chloride; triethylamine / diethyl ether / 1 h / -30 °C
6.2: 80 percent / tetrahydrofuran; diethyl ether / 1 h / 0 °C
7.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C
7.2: 0.147 g / Davis' oxaziridine / tetrahydrofuran / 0.08 h / -84 °C
With
1H-imidazole; sodium periodate; hydrogen; iodine; sodium hexamethyldisilazane; pivaloyl chloride; triethylamine; triphenylphosphine;
ruthenium trichloride; palladium/alumina;
In
tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; water; acetonitrile;
3.2: Wittig olefination;
DOI:10.1002/ejoc.200600113