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

HRID 542920

Reaction equation

HRID 542920 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](Cl)(Cl)(Cl)(Cl)Cl>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 24294Antimony pentachloride

Product 1

HCID 140270alpha-L-Sorbofuranose, 2,3:4,6-bis-o-(1-methylethylidene)-Yield 170.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
61 °C

Procedure

To 200 ml of acetone were added 10.0 g of L-sorbose and 89.7 mg of antimony pentachloride, and the mixture was refluxed with stirring in a water bath of 61° C. for 8 hours. During this reaction, the refluxing solvent was dried with 35 g of Molecular Sieves 3A interposed between the reaction vessel and the condenser. After completion of the reaction, the total volume of the reaction mixture was adjusted to 200 ml, and the quantitative analysis by gas chromatography (column: 3% Silicon OV-17, on Uniport HPS 3m, column temperature; 160° C.) indicated that there was obtained 12.29 g (85.1%) 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 35 g of Molecular Sieves 3A
  4. customAfter completion of the reaction

Sources & evidence

ORD record
ord-7f2157f769ba468bb88d73906b7c7c6b
Source dataset
uspto-grants-1987_04
Patent number
US04659809

Linked notes

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