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Acetic Anhydride → L-Galactose, 6-deoxy-, 2,3,4,5-tetraacetate

HRID 1155323
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Reaktionsgleichung

Reaktionsgleichung von HRID 1155323
[O:1]=[CH:2][C@H:3]([C@@H:5]([C@@H:7]([C@H:9]([CH3:11])[OH:10])[OH:8])[OH:6])[OH:4].C(O[C:16](=[O:18])[CH3:17])(=O)C>>[C:2]([O:4][C@@H:3]([C@@H:5]([C@@H:7]([C@H:9]([CH3:11])[O:10][C:16](=[O:18])[CH3:17])[O:8][C:9](=[O:10])[CH3:11])[O:6][C:5](=[O:6])[CH3:7])[CH:2]=[O:1])(=[O:1])[CH3:3]
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Komponenten

3

Edukt 2

HCID 7918Acetic AnhydrideHCID 3034656L-(-)-Fucose

Produkt 1

HCID 14701098L-Galactose, 6-deoxy-, 2,3,4,5-tetraacetate

Versuchsvorschrift

L-Fucose is then acetylated with acetic anhydride to produce fucose tetraacetate. Preferably, the reaction is carried out by suspending the L-fucose in a solvent, such as pyridine, and slowly adding the acetic anhydride. The mixture is stirred, poured into a separating funnel containing ice water, and extracted with chloroform. The organic extracts are washed with water, aqueous sodium bicarbonate, and dried over magnesium sulfate. The mixture is filtered and the solvent removed under reduced pressure. The residue is co-evaporated with toluene to remove any remaining pyridine or acetic acid. The fucose tetraacetate is then brominated to produce 2,3,4-tri-O-acetyl-L-fucopyranosyl bromide having the formula: ##STR13## It is to be noted that in the above formula, and elsewhere herein, the use of "Ac" is understood to represent the acetyl radical, i.e., ##STR14## The fucose tetraacetate is brominated with hydrogen bromide in acetic acid. The mixture is worked up similarly to that just described for preparing fucose tetraacetate, i.e., chloroform extraction from ice water.

Quellen und Nachweise

ORD-Eintrag
ord-06b3c453037545ab9842973020f30e1e
Quelldatensatz
uspto-grants-1981_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04301276

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