Acetone → 2,3:5,6-Di-O-isopropylidene-alpha-D-mannofuranose

HRID 358131Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 358131
[CH3:1][C:2]([CH3:4])=[O:3].O=[CH:6][C@H:7]([C@H:9]([C@@H:11]([C@@H:13]([CH2:15][OH:16])[OH:14])[OH:12])[OH:10])[OH:8].I.N1C=C[CH:21]=[CH:20][CH:19]=1>>[CH3:1][C:2]1([CH3:4])[O:8][C@@H:7]([C@H:9]2[O:10][C@H:15]([OH:16])[C@H:13]3[O:14][C:20]([CH3:21])([CH3:19])[O:12][C@@H:11]23)[CH2:6][O:3]1

Komponenten

5

Edukt 4

HCID 180AcetoneHCID 1049PyridineHCID 24841Hydrogen iodideHCID 161658Demannose

Produkt 1

HCID 71571882,3:5,6-Di-O-isopropylidene-alpha-D-mannofuranoseAusbeute 80 %

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To 200 ml of acetone were added 10.0 g of D-mannose and 100 mg of hydrogen iodide and the mixture was refluxed with stirring in a water bath at 60° C.for 5 hours. During this reaction, the refluxing solvent was dried with 20 g of Molecular Sieves 3A interposed between the reaction vessel and the cooling jacket. After completion of the reaction, a small amount of pyridine was added. The acetone was then distilled off under reduced pressure and the residue was dissolved in benzene, washed with aqueous sodium bicarbonate and water and dried over anhydrous magnesium sulfate. The benzene was distilled off under reduced pressure to give 11.5 g (80%) of 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose. After recrystallization from petroleum ether, it melted at 122°-123° C.

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. customDuring this reaction
  3. dry with materialthe refluxing solvent was dried with 20 g of Molecular Sieves 3A
  4. customAfter completion of the reaction
  5. distillationThe acetone was then distilled off under reduced pressure
  6. dissolutionthe residue was dissolved in benzene
  7. washwashed with aqueous sodium bicarbonate and water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe benzene was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-291c44cfc18946fcb3ccda5d5e62eb6d
Quelldatensatz
uspto-grants-1984_08
Patentnummer
US04464530

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