Reaktion #336548

ord-881e0900f41e437f820932ab56a9cc92

Reaktionsgleichung

CCOC(=O)[C@@H]1OS(=O)O[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C
ethyl (4R,5R)-5-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]-1,3,2-dioxathiolane-4-carboxylate-2-oxide
CCOC(=O)[C@H](O)[C@@H](O)C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C
ethyl (2R,3R)-2,3-dihydroxy-3-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]propionate
→
CCOC(=O)[C@@H]1OS(=O)(=O)O[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C
target compound
CCOC(=O)[C@@H]1OS(=O)(=O)O[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C
Ethyl (4R,5R)-5-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]-1,3,2-dioxathiolane-4-carboxylate-2,2-dioxide

Edukte

CCOC(=O)[C@@H]1OS(=O)O[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C
ethyl (4R,5R)-5-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]-1,3,2-dioxathiolane-4-carboxylate-2-oxide
CCOC(=O)[C@H](O)[C@@H](O)C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C
ethyl (2R,3R)-2,3-dihydroxy-3-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]propionate

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Following the same procedures as in Example 3, ethyl (4R,5R)-5-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]-1,3,2-dioxathiolane-4-carboxylate-2-oxide was prepared from ethyl (2R,3R)-2,3-dihydroxy-3-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]propionate (40 mg). Subsequently, 30 mg of a target compound were obtained following the same procedures as in Example 4. NMR data of the compound were as follows.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05214056uspto-grants-1993_05