Cyclohexanone → 2,3:5,6-DI-O-Cyclohexylidene-alpha-D-mannofuranose

HRID 1462588Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1462588
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O=[CH:9][C@H:10]([C@H:12]([C@@H:14]([C@@H:16]([CH2:18][OH:19])[OH:17])[OH:15])[OH:13])[OH:11]>ClCCl>[CH2:4]1[CH2:5][CH2:6][C:1]2([O:11][C@@H:10]([C@H:12]3[O:13][C@@H:18]4[O:19][C:1]5([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)[O:17][C@H:16]4[C@H:14]3[OH:15])[CH2:9][O:7]2)[CH2:2][CH2:3]1

Komponenten

4

Edukt 2

HCID 7967CyclohexanoneHCID 161658Demannose

Produkt 1

HCID 904740782,3:5,6-DI-O-Cyclohexylidene-alpha-D-mannofuranoseAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixed solution of 150 ml of cyclohexanone and 120 ml of dichloromethane were added 10.0 g of D-mannose and 125 mg of anhydrous cupric chloride, and the mixture was stirred for 9 hours under reflux in a warm-water bath at 63° to 65° C. The refluxing solvent was continuously dried with 20 g of molecular sieves 3A which was placed between the reaction vessel and cooling tube. The reaction solution was diluted with benzene, washed with aqueous sodium hydrogencarbonate and water, and dried over anhydrous magnesium sulfate. When the solvent and cyclohexanone were distilled off under reduced pressure, there was obtained 17.9 g (95%) of 2,3:5,6-di-O-cyclohexylidene-α-D-mannofuranose (purity of not less than 95%) as a residue. The compound, when recrystallized from n-hexane, showed a melting point of 122° to 124° C.

Aufarbeitung

  1. temperatureunder reflux in
  2. temperaturea warm-water bath at 63° to 65° C
  3. dry with materialThe refluxing solvent was continuously dried with 20 g of molecular sieves 3A which
  4. temperaturecooling tube
  5. additionThe reaction solution was diluted with benzene
  6. washwashed with aqueous sodium hydrogencarbonate and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationWhen the solvent and cyclohexanone were distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-99f7fb2e7d9543068875b7f660a82b2c
Quelldatensatz
uspto-grants-1984_07
Patentnummer
US04460767

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