Methanol → Methyl glucoside

HRID 2119196Notes

Reaction equation

HRID 2119196 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].FS(O)(=O)=O.[CH3:18]O>O>[CH3:18][O:1][C@H:2]1[O:10][CH:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@@H:5]([OH:6])[C@@H:3]1[OH:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 24603Fluorosulfuric acid2×HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 76607Methyl glucoside

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In an autoclave of 300 cc volume, 50 g of anhydrous crystalline glucose, 5 g of perfluorosulfonic acid resin ("NAFION" powder 511) and 133 g of methyl alcohol were charged. The reaction was effected at 120° C.±1° C. for 30 minutes while stirring at 600 r.p.m. The gauge pressure was 6.0 Kg/cm2. After cooling to room temperature, NAFION was separated by filtration whereby a colorless, transparent methanolic solution was obtained. By adding water and evaporating methanol at 40° C. under reduced pressure, an aqueous methyl glucoside solution was obtained. The aqueous solution was essentially colorless and transparent and 53.6 g of solid matters were contained therein. By liquid chromatography and enzymatic method, the composition of the solid matters was found to be the following:

Workup

  1. customNAFION was separated by filtration whereby a colorless, transparent methanolic solution
  2. customwas obtained
  3. customevaporating methanol at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-d5d71c82c1ba493bb11a1fe1653e4ee5
Source dataset
uspto-grants-1987_07
Patent number
US04683297

Reaction notes

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