alpha-D-Xylofuranose, 1,2:3,5-bis-O-(1-methylethylidene)- → 1,2-O-isopropylidene-alpha-D-xylofuranose

HRID 51256

Reaction equation

HRID 51256 reaction equation
CC1(C)[O:7][C@@H:6]2[C@H:8]3[O:13][C:12]([CH3:15])([CH3:14])[O:11][C@H:9]3[O:10][C@@H:5]2[CH2:4][O:3]1.O=C[C@@H]([C@H]([C@@H](CO)O)O)O>OS(O)(=O)=O>[CH3:14][C:12]1([CH3:15])[O:11][C@@H:9]2[C@@H:8]([C@@H:6]([OH:7])[C@@H:5]([CH2:4][OH:3])[O:10]2)[O:13]1

Participants

4

Reactant 2

HCID 30337alpha-D-Xylofuranose, 1,2:3,5-bis-O-(1-methylethylidene)-HCID 644160aldehydo-D-Xylose

Product 1

HCID 883381,2-O-isopropylidene-alpha-D-xylofuranoseYield 70.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

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.

Workup

  1. customthe reaction is quenched with NH4OH (pH 9.0) and half of the water
  2. customremoved at reduced pressure
  3. additionThe aqueous layer is diluted with brine (100 mL)
  4. extractionextracted with ethyl acetate (3×200 mL)
  5. customA normal work-up provides an oil
  6. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-86c0af43d04f425b9c521d471668ebcb
Source dataset
uspto-grants-2004_03
Patent number
US06713627B2

Linked notes

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