Trichloroacetonitrile → 2,3,4-tri-O-acetyl-5-thio-alpha-D-xylopyranosyl trichloroacetimidate

HRID 6031

Reaktionsgleichung

Reaktionsgleichung von HRID 6031
[Cl:1][C:2]([Cl:6])([Cl:5])[C:3]#[N:4].[H-].[Na+].[C:9]([O:12][C@@H:13]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:18]([O:24][C:25](=[O:27])[CH3:26])[CH2:17][S:16][C@@H:14]1[OH:15])(=[O:11])[CH3:10]>C(Cl)Cl>[Cl:1][C:2]([Cl:6])([Cl:5])[C:3](=[NH:4])[O:15][C@H:14]1[S:16][CH2:17][C@@H:18]([O:24][C:25](=[O:27])[CH3:26])[C@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:13]1[O:12][C:9](=[O:11])[CH3:10]

Komponenten

5

Edukt 3

HCID 11011TrichloroacetonitrileHCID 24758Sodium hydrideHCID 232401882,3,4-tri-O-acetyl-5-thio-alpha-D-xylopyranose

Produkt 1

HCID 216315472,3,4-tri-O-acetyl-5-thio-alpha-D-xylopyranosyl trichloroacetimidateAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.5 ml (15.10-3 mol) of trichloroacetonitrile and 70 mg of NaH (2.3.10-3 mol of NaH in 80% dispersion) are added to a solution of 1 g (3.42.10-3 mol) of 2, 3, 4 -tri-O-acetyl-5-thio-α-D-xylopyranose in 10 ml of methylene chloride. After 4 h at room temperature, the reaction medium is filtered on silica in methylene chloride and then purified by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent. 790 mg (yield: 53%) of the expected product are obtained after crystallization from an ethyl acetate/hexane mixture.

Aufarbeitung

  1. filtrationthe reaction medium is filtered on silica in methylene chloride
  2. custompurified by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-aa359b71c3c249e1a1f6ac726e50d826
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246961

Verknüpfte Notizen

Wird geladen…