Methyl 3-deoxy-3-fluoro-beta-D-allopyranoside → GlyTouCan:G23553KL
Reaktionsgleichung
[F:1][C@@H:2]1[C@H:9]([OH:10])[C@@H:8]([CH2:11][OH:12])[O:7][C@@H:4]([O:5]C)[C@@H:3]1[OH:13]>Cl.O>[F:1][C@@H:2]1[C@H:9]([OH:10])[C@@H:8]([CH2:11][OH:12])[O:7][CH:4]([OH:5])[C@@H:3]1[OH:13]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
Methyl 3-deoxy-3-fluoro-β-D-allopyranoside (24.5 g) [compound (1); this compound is described in "J. Org. Chem.", 48, pp. 4734-4743 (1983) by Peter J. Card et al.] was dissolved in 6M hydrochloric acid (500 ml) and the solution was allowed to stand at 70° C. for 8 hours (for hydrolysis reaction). The resulting reaction solution was concentrated and the syrup so obtained was dissolved in water (400 ml). The solution was neutralized with addition of ion-exchange resin, Dowex 1×2(OH- form) (100-200 mesh) (apparently 800 ml), then filtered and the filtrate was concentrated to afford the titled compound (2) (22.1 g) as a colorless syrup. Yield: 97%.