Acetic Acid → 2',3'-Didehydro-2',3'-dideoxycytidine

HRID 864279

Reaktionsgleichung

Reaktionsgleichung von HRID 864279
[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13]([NH2:14])=[N:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3](O)[CH2:2]1.[OH-].[Na+].C(O)(=O)C.CC(C)([O-])C.[K+]>C(O)C.CS(C)=O>[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13]([NH2:14])=[N:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[CH:3]=[CH:2]1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 13711DeoxycytidineHCID 14798Sodium HydroxideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 646832',3'-Didehydro-2',3'-dideoxycytidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

Namely, 2',3'-dideoxycytidine can be obtained according to the method of Horwitz et al in a way that N-benzoyl-2'-deoxy-3',5'-di-0-mesylcytidine derivable from 2'-deoxycytidine is refluxed with aqueous solution of sodium hydroxide in ethanol, then this is treated with dilute acetic acid, and further allowed to react with potassium tert-butoxide in dimethyl sulfoxide to obtain 2',3'-dideoxy-2',3'-didehydrocytidine, which is hydrogenated (J. Org. Chem., 32, 817, 1967).

Quellen und Nachweise

ORD-Eintrag
ord-26168c6f4eb240088b28307454eac529
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05563049

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