Chloroform → 2,3,4-Tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-beta-D-galactopyranose

HRID 1105876

Reaktionsgleichung

Reaktionsgleichung von HRID 1105876
C(Cl)(Cl)Cl.[C:5]([O:8][C@@H:9]1[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@@H:13]([O:19][C:20](=[O:22])[CH3:21])[C@@H:12]([CH2:23][N:24]2[C:28](=[O:29])[C:27]3=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]3[C:25]2=[O:34])[O:11][C@H:10]1[S:35]C(=N)N)(=[O:7])[CH3:6].S(S([O-])=O)([O-])(=O)=O.[K+].[K+]>O>[C:5]([O:8][C@@H:9]1[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@@H:13]([O:19][C:20](=[O:22])[CH3:21])[C@@H:12]([CH2:23][N:24]2[C:28](=[O:29])[C:27]3=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]3[C:25]2=[O:34])[O:11][C@H:10]1[SH:35])(=[O:7])[CH3:6]

Komponenten

5

Edukt 3

HCID 6212ChloroformHCID 28019Potassium MetabisulfiteHCID 228184952-S-(2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-beta-D-galactopyranosyl)-2-thiopseudourea

Produkt 1

HCID 128055222,3,4-Tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-beta-D-galactopyranoseAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Chloroform (9.0 ml.) is added to a solution of 2-S-(2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-β-D-galactopyranosyl)-2-thiopseudourea (3.4 g.) in water (10 ml.) containing potassium metabisulfite (1.38 g.). The mixture is heated with stirring under reflux for 15 minutes. The cooled solution is separated, and the organic layer is dried and evaporated in vacuo to give the title compound (2.5 g.). This material is used directly for the preparation of 6-(5-cholesten-3β-yloxy)hexyl 2,3,4-tri-O-acetyl-6-deoxy-6-ththalimido-1-thio-β-D-galactopyranoside

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 15 minutes
  3. customThe cooled solution is separated
  4. customthe organic layer is dried
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3e1c7af0f3954cafb88e31b24631eea3
Quelldatensatz
uspto-grants-1982_01
Patentnummer
US04310505

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