4-O-Benzyl-2-deoxy-2-C-hydroxymethyl-D-glucopyranose → 4-O-Benzyl-2-deoxy-2-C-hydroxymethyl-D-xylo-pentodialdose

Temperature

45 °C

To a solution of 4-O-benzyl-2-deoxy-2-C-hydroxymethyl-D-gluco-pyranose (1.41 g, 5.0 mmol) in methanol (15 ml), a solution of sodium periodate (5.35 g, 25.0 mmol) in water (50 ml) was added dropwise over 15 minutes. Further, methanol (25 ml) was added. The mixture was stirred at 45° C. for 3 hours. The precipitated iodate was filtered off, and the mixture was concentrated. By resolution of the residue in ethyl acetate/ethanol (1:1; 80 ml), more iodate was precipitated and filtered off. The mother liquour was concentrated and the residue (2.07 g) was flash chromatographed using ethyl acetate as eluent. The purified product was obtained as a yellow sirup in 87% (1.09 g) yield and 9% of unreacted starting material (0.13 g) was isolated. The purified product was used imidiately in the next reaction.

1. filtrationThe precipitated iodate was filtered off
2. concentrationthe mixture was concentrated
3. customBy resolution of the residue in ethyl acetate/ethanol (1:1; 80 ml), more iodate was precipitated
4. filtrationfiltered off
5. concentrationThe mother liquour was concentrated
6. customchromatographed
7. customThe purified product was obtained as a yellow sirup in 87% (1.09 g)
8. customyield
9. customwas isolated
10. customThe purified product was used imidiately in the next reaction

ORD record

ord-ffd55edcae694ef0a83c4fea4814932a

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05863903