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

HRID 2293653Notes

Reaction equation

HRID 2293653 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 20.9 g of methyl b-D-glucofuranosidurono-6,3-lactone (MbGlucl). By further concentration of the filtrate an additional 28.2 g of MbGlucl was isolated giving a total yield of 49.1 g (45.3%), MP=139° C., purity=99.1% (GC).

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-37895ab5da644e58844d2ed136c622c7
Source dataset
uspto-grants-1997_11
Patent number
US05686603

Reaction notes

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