L-(-)-Sorbose → alpha-L-Sorbofuranose, 2,3:4,6-bis-o-(1-methylethylidene)-

HRID 542921Notes

Reaction equation

HRID 542921 reaction equation
[OH:1][CH2:2][C:3]([C@H:5]([C@@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])=[O:4].[Sb](F)(F)(F)(F)F>CC(C)=O>[CH3:2][C:3]1([CH3:5])[O:6][CH:5]2[CH:7]3[O:8][C:9]([CH3:11])([CH3:7])[O:10][C:9]3([CH2:11][OH:12])[O:4][CH:3]2[CH2:2][O:1]1

Participants

4

Reactant 2

HCID 6904L-(-)-SorboseHCID 24557Antimony pentafluoride

Product 1

HCID 140270alpha-L-Sorbofuranose, 2,3:4,6-bis-o-(1-methylethylidene)-Yield 164.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To 200 ml of acetone were added 10.0 g of L-sorbose and 65.0 mg of antimony pentafluoride, and the mixture was refluxed with stirring in a water bath of 60° C. for 6 hours. During this reaction, the refluxing solvent was dried with 20 g of Molecular Sieves 3A interposed between the reaction vessel and the condenser. The quantitative analysis of the reaction solution according to the same procedure as described in Example 14 showed that there was obtained 11.89 g (82.3%) of 2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose.

Workup

  1. temperaturethe mixture was refluxed
  2. customDuring this reaction
  3. dry with materialthe refluxing solvent was dried with 20 g of Molecular Sieves 3A

Sources & evidence

ORD record
ord-a73e3fa2ba72475993941e866dc825e4
Source dataset
uspto-grants-1987_04
Patent number
US04659809

Reaction notes

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