Methanol → Phenyl beta-D-galactopyranoside

HRID 1250759Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1250759
CC([O:4][CH2:5][C@H:6]1[O:11][C@@H:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:9]([O:19]C(C)=O)[C@@H:8]([O:23]C(C)=O)[C@H:7]1[O:27]C(C)=O)=O.CO.C[O-].[Na+]>C(O)(=O)C>[CH:16]1[CH:15]=[CH:14][C:13]([O:12][C@@H:10]2[O:11][C@H:6]([CH2:5][OH:4])[C@H:7]([OH:27])[C@H:8]([OH:23])[C@H:9]2[OH:19])=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 102346Phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosideHCID 10942334Sodium Methoxide

Produkt 1

HCID 102336Phenyl beta-D-galactopyranosideAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To phenyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (21.2 g) were added methanol (120 ml) and 28% sodium methylate (0.28 ml) and the mixture was refluxed with stirring for 5 hours. After the reaction solution was cooled, acetic acid (0.1 ml) was added and the mixture was stirred for 30 minutes. Concentration of the reaction solution and crystallization with ethanol (180 ml) gave 9.8 g (yield 77%) of phenyl-β-D-galactopyranoside. Melting point: 154.5° C.

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. temperatureAfter the reaction solution was cooled
  3. stirringthe mixture was stirred for 30 minutes
  4. customConcentration of the reaction solution and crystallization with ethanol (180 ml)

Quellen und Nachweise

ORD-Eintrag
ord-f26a427a205947ca8efaa64c8cab0541
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06339162B1

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