Acetic Acid → alpha-D-Glucopyranosyl bromide, tetraacetate

Temperatur

18 °C

1,2,3,4,6-Penta-O-acetyl-β-D-glucopyranose (100 g, 0.251 mol) is suspended in toluene (210 ml). Acetic anhydride (9.5 ml; 0.1 mol) is added followed by hydrobromic acid 30% in acetic acid (200 ml, 1 mol). The mixture is stirred at 18° C. for 30 min. A mixture of ice/water (300 ml) and brine (100 ml) is then added with stirring. The phases are separated and the aqueous phase is extracted with toluene (100 ml). The organic phases are combined and washed with aqueous sodium hydrogencarbonate (100 ml) and brine (100 ml). Drying and evaporation of the solvent under reduced pressure yields an oil which is crystallised by addition of methyl-t-butylether (150 ml) and methylcyclohexane (300 ml). The product is isolated by filtration, washed with methylcyclohexane and dried under vacuo at 45° C.

1. additionis then added
2. stirringwith stirring
3. customThe phases are separated
4. extractionthe aqueous phase is extracted with toluene (100 ml)
5. washwashed with aqueous sodium hydrogencarbonate (100 ml) and brine (100 ml)
6. customDrying
7. customevaporation of the solvent under reduced pressure
8. customyields an oil which
9. customis crystallised by addition of methyl-t-butylether (150 ml) and methylcyclohexane (300 ml)
10. customThe product is isolated by filtration
11. washwashed with methylcyclohexane
12. customdried under vacuo at 45° C.

ORD-Eintrag

ord-d41467ce60e84aa2a40f2ccbcbb749f5

Quelldatensatz

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07838500B2