Benzyl Alcohol → Benzyl 2-deoxy-beta-D-glucopyranoside

HRID 276096

Reaktionsgleichung

Reaktionsgleichung von HRID 276096
[O:1]=[CH:2][CH2:3][C@H:4]([C@@H:6]([C@@H:8]([CH2:10][OH:11])[OH:9])[OH:7])[OH:5].[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[O:1]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C@@H:2]1[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[CH2:3]1

Komponenten

3

Edukt 2

HCID 244Benzyl AlcoholHCID 1082232-Deoxyglucose2×

Produkt 1

HCID 53805352Benzyl 2-deoxy-beta-D-glucopyranosideAusbeute 69 %

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-deoxy-D-glucose (Compound 1a, 2.5 g, 15.2 mmol) was dissolved in benzyl alcohol (20 mL), and then Dowex® 50W-X8 (H+ form, 3.5 g) was added. The reaction solution was stirred at 60° C. for 24 hours. Then the resin was filtered off, and the product was purified by flash column chromatography with CHCl3—MeOH (15:1) to give Compound 1 (2.67 g, 10.5 mmol) in 69 percent yield.

Aufarbeitung

  1. addition(H+ form, 3.5 g) was added
  2. filtrationThen the resin was filtered off
  3. customthe product was purified by flash column chromatography with CHCl3—MeOH (15:1)

Quellen und Nachweise

ORD-Eintrag
ord-fb178818687e467dbdc84d38697bac2b
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353095B1

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