Ethyl D-glucopyranoside → Ethyl glucoside, alpha-

HRID 1612916Notes

Reaction equation

HRID 1612916 reaction equation
[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]>C([O-])(=O)C>[O:1]([CH2:13][CH3:14])[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]

Participants

3

Reactant 1

HCID 11127487Ethyl D-glucopyranoside

Product 1

HCID 9815668Ethyl glucoside, alpha-Yield 55%

Reagents, catalysts & solvents 1

HCID 175AcetateSolvent

Procedure

Ethyl D-glucopyranoside (30 g, prepared as described in example 10) with an anomeric ratio α:β=1:1 was dissolved in 0.05M acetate buffer (400 ml, pH 4.5) at 30° C. β-glucosidase (50 mg from almonds, Sigma) was added and the mixture was stirred for a week. The solution was evaporated in vacuo and purified by chromatography to give the product as a crystalline solid (8.2 g, 55%).

Workup

  1. additionwas added
  2. customThe solution was evaporated in vacuo
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-01368e5221014e0092f126592ddc06b7
Source dataset
uspto-grants-1993_03
Patent number
US05191071

Reaction notes

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