Ethanol → Ethyl D-glucopyranoside

HRID 1612913Notes

Reaction equation

HRID 1612913 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].[CH2:13](O)[CH3:14]>>[O:1]([CH2:13][CH3:14])[CH:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]

Participants

3

Reactant 2

HCID 702EthanolHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 11127487Ethyl D-glucopyranoside

Conditions

Temperature
80 °C

Procedure

Glucose (500 g, 2.78 mol) and a strong acid cation exchange resin (100 g Amberlyst™ 15, BDH Chemicals) was suspended in ethanol (2000 ml, 34.3 mol) The mixture was stirred at 80° C. for 16 hours. The progress of the reaction was followed by HPLC. The ion exchange resin was removed by filtration and the solution was treated with activated carbon (10 g). After filtration the ethanol was removed in vacuo giving ethyl D-glucopyranoside (a 1:1 mixture of α and β anomers) as a syrup (578 g, quantitative yield).

Workup

  1. customThe ion exchange resin was removed by filtration
  2. additionthe solution was treated with activated carbon (10 g)
  3. filtrationAfter filtration the ethanol
  4. customwas removed in vacuo

Sources & evidence

ORD record
ord-8c9e8f0b84f649d3869183c2a0e14ad0
Source dataset
uspto-grants-1993_03
Patent number
US05191071

Reaction notes

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