Methanol → 6082-04-8

HRID 1840255Notes

Reaction equation

HRID 1840255 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:11]([OH:12])[C@H:10]([OH:13])[C@@H:9]([CH2:14][OH:15])[O:8][CH:6]1[OH:7])(=[O:3])[CH3:2].[CH3:16]O>>[C:1]([NH:4][C@@H:5]1[C@@H:11]([OH:12])[C@H:10]([OH:13])[C@@H:9]([CH2:14][OH:15])[O:8][C@@H:6]1[O:7][CH3:16])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 887MethanolHCID 439174N-Acetyl-D-Glucosamine

Product 1

HCID 965236082-04-8Yield 25%

Procedure

To a solution of N-acetylglucosamine (50 g, 0.22 mmol) in MeOH (50 ml), a catalytic quantity of Amberlite IR-120 H+ resin is added, and the mixture is heated for 2 days. The mixture is filtered, concentrated and purified by silica gel column chromatography (CH2Cl2/MeOH 5:1), obtaining 10 g of the α-anomer methyl 2-acetamido-2-deoxy-α-D-glucopyranoside (25%) anomer and 40 g of the β-anomer that is isomerised to give the α-anomer methyl 2-acetamido-2-deoxy-α-D-glucopyranoside in the same reaction conditions (70% yield).

Workup

  1. temperaturethe mixture is heated for 2 days
  2. filtrationThe mixture is filtered
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography (CH2Cl2/MeOH 5:1)

Sources & evidence

ORD record
ord-265c83d531274743ac79e874b32df4dd
Source dataset
uspto-grants-2004_01
Patent number
US06680304B2

Reaction notes

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