Methanol → methyl b-D-glucofuranosidurono-6,3-lactone

HRID 36061Notes

Reaction equation

HRID 36061 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]1[O:12][C:10](=[O:11])[C@@H:8]([OH:9])[C@H:6]1[OH:7])[OH:4].[CH3:13]O.[OH-].[K+]>CS(O)(=O)=O>[O:11]([CH3:13])[C@@H:10]1[O:12][C@@H:5]2[C@@H:3]([C:2]([O:7][C@@H:6]2[C@H:8]1[OH:9])=[O:1])[OH:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 92283Glucuronolactone

Product 1

HCID 11805515methyl b-D-glucofuranosidurono-6,3-lactoneYield 19.3%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidCatalyst

Procedure

D-Glucurono-6,3-lactone (100.0 g, 0.57 mole), anhydrous methanol (200.0 g, 6.24 moles), and methanesulfonic acid (3 drops) were placed in an oven dried three-necked round bottom flask equipped with mechanical stirrer, thermometer and condenser. The mixture was heated for 24 hours at reflux, cooled and neutralized with 0.1N methanolic KOH. The mixture was filtered and washed with cold methanol (20 ml) yielding 20.9g of methyl β-D-glucofuranosidurono-6, 3-lactone (MβGlucl). By further concentration of the filtrate an additional 28.2 g of MβGlucl was isolated giving a total yield of 49.1 g (45.3%), MP=139, % Purity=99.1.

Workup

  1. customequipped with mechanical stirrer
  2. temperatureThe mixture was heated for 24 hours
  3. temperatureat reflux
  4. temperaturecooled
  5. filtrationThe mixture was filtered
  6. washwashed with cold methanol (20 ml)

Sources & evidence

ORD record
ord-cf15b780d0e5404789b80b8d842efd0d
Source dataset
uspto-grants-1995_05
Patent number
US05412118

Reaction notes

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