Reaktion #79534

ord-86c0af43d04f425b9c521d471668ebcb

Reaktionsgleichung

CC1(C)OC[C@H]2O[C@@H]3OC(C)(C)O[C@@H]3[C@H]2O1
1,2:3,5-Di-O-isopropylidene-D-xylofuranose
O=C[C@H](O)[C@@H](O)[C@H](O)CO
xylose
→
CC1(C)O[C@H]2O[C@H](CO)[C@H](O)[C@H]2O1
1,2-O-isopropylidene-D-xylofuranose
Ausbeute 70.1%

Edukte

CC1(C)OC[C@H]2O[C@@H]3OC(C)(C)O[C@@H]3[C@H]2O1
1,2:3,5-Di-O-isopropylidene-D-xylofuranose
O=C[C@H](O)[C@@H](O)[C@H](O)CO
xylose

Reagenzien

Keine

Lösungsmittel

O=S(=O)(O)O
H2SO4

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe reaction is quenched with NH4OH (pH 9.0) and half of the water
  2. 2
    Sonstigeremoved at reduced pressure
  3. 3
    workup.ADDITIONThe aqueous layer is diluted with brine (100 mL)
  4. 4
    Extraktionextracted with ethyl acetate (3×200 mL)
  5. 5
    SonstigeA normal work-up provides an oil
  6. 6
    workup.DISTILLATIONKugelrohr distillation

Vorschrift

1,2:3,5-Di-O-isopropylidene-D-xylofuranose (70.66 g, 0.30 mol) is treated with H2SO4 (0.1 M, 300 mL). Upon stirring, the xylose slowly dissolves. After 30 minutes, the reaction is quenched with NH4OH (pH 9.0) and half of the water removed at reduced pressure. The aqueous layer is diluted with brine (100 mL) and extracted with ethyl acetate (3×200 mL). A normal work-up provides an oil. Kugelrohr distillation provides 1,2-O-isopropylidene-D-xylofuranose (40 g, 68.5%); b.p. 120-135° C./0.4 mm Hg.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06713627B2uspto-grants-2004_03