Acetic Anhydride → alpha-D-Glucopyranosyl pentaacetate

HRID 1279149Notes

Reaction equation

HRID 1279149 reaction equation
[OH:1][C@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7](O)[C@H:5]([OH:6])[C@H:3]1O.[C:13]([O:16][C:17](=[O:19])[CH3:18])(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([O:16][C@H:17]1[O:19][C@H:7]([CH2:5][O:6][C:11](=[O:12])[CH3:9])[C@@H:9]([O:10][C:2](=[O:1])[CH3:3])[C@H:11]([O:12][C:5](=[O:6])[CH3:7])[C@H:18]1[O:10][C:2](=[O:1])[CH3:3])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 79025Alpha-D-Glucose

Product 1

HCID 2723636alpha-D-Glucopyranosyl pentaacetateYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Analogously, as described in the synthesis of title compound Aa), the reaction of 100 g (555.0 mmol) of α-D-glucopyranose with a mixture of 1000 ml of absolute pyridine and 1000 ml of acetic acid anhydride after working-up and recrystallization from 95% aqueous ethanol yields 190.6 g (88.0%) of the above-mentioned title compound as a colorless and crystalline compound. By 1H-NMR-spectroscopic study of the title compound that is thus obtained, it was possible to determine the α to β-ratio of two possible anomers with ≧98:2. Accordingly, the title compound is the exclusively α-configured anomer.

Workup

  1. customrecrystallization from 95% aqueous ethanol

Sources & evidence

ORD record
ord-452fc11b03e643f3b000291e3c842f68
Source dataset
uspto-grants-2002_09
Patent number
US06447749B1

Reaction notes

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