Methanol → Methyl D-glucoside

HRID 1589780Notes

Reaction equation

HRID 1589780 reaction equation
[OH:1][C@H: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].[CH3:13]O>>[O:1]([CH3:13])[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 887MethanolHCID 79025Alpha-D-Glucose

Product 1

HCID 3036743Methyl D-glucosideYield 57%

Conditions

Temperature
65 °C

Procedure

α-D-glucose (500 g, 2.78 mol) and a strongly acidic cation exchange resin (100 g Amberlyst 15, BDH Chemicals) was suspended in methanol (1500 ml, 37.1 mol). The mixture was stirred at 65° C. for 68 hours. The progress of the reaction was followed by HPLC. 1H NMR analysis of the reaction mixture showed a 1:1 ratio of the α-and β-anomers. The ion exchange resin was removed by filtration and the solution was cooled to 4° C. The crystalline methyl α-D-glucopyranoside was removed by filtration (230 g, 43%) and the mother liquor was evaporated in vacuo to give a crude methyl D-glucopyranoside (304 g, 57%) as a thick syrup (1H NMR showed a ratio between α- and β-anomers of 2/3).

Workup

  1. customThe ion exchange resin was removed by filtration
  2. temperaturethe solution was cooled to 4° C
  3. customThe crystalline methyl α-D-glucopyranoside was removed by filtration (230 g, 43%)
  4. customthe mother liquor was evaporated in vacuo

Sources & evidence

ORD record
ord-00fd638c0d41464696bea49aa4c5a664
Source dataset
uspto-grants-1993_04
Patent number
US05200328

Reaction notes

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