Acetic Anhydride → 1,2:5,6-Bis-O-(1-methylethylidene)-alpha-D-allofuranose

HRID 25471

Reaktionsgleichung

Reaktionsgleichung von HRID 25471
[CH3:1][C:2]1([CH3:18])[O:6][C@@H:5]([C@H:7]2[O:11][C@@H:10]3[O:12][C:13]([CH3:16])([CH3:15])[O:14][C@@H:9]3[C@H:8]2[OH:17])[CH2:4][O:3]1.C(OC(=O)C)(=O)C.[BH4-].[Na+]>CS(C)=O>[CH3:1][C:2]1([CH3:18])[O:6][C@@H:5]([C@H:7]2[O:11][C@@H:10]3[O:12][C:13]([CH3:16])([CH3:15])[O:14][C@@H:9]3[C@@H:8]2[OH:17])[CH2:4][O:3]1

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 4311764Sodium borohydrideHCID 7067560Diacetone-D-glucose

Produkt 1

HCID 71570541,2:5,6-Bis-O-(1-methylethylidene)-alpha-D-allofuranose

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

In a preferred embodiment of the method according to the invention, 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose is reacted with a mixture of DMSO and acetic anhydride in a molar ratio of 1:3 to 1:9 at 20-25° C., for around 12-48 h, typically for around 24 h, followed by reaction with sodium borohydride at 20-25° C., for around 0.5-2 h, typically for around 1 h, in order to yield 1,2:5,6-di-O-isopropylidene-α-D-allofuranose. The two reactions are performed sequentially, i.e. without isolation or purification of the intermediate product, i.e. the ulose.

Quellen und Nachweise

ORD-Eintrag
ord-0d4371ae6e2f49a3b0482815d240bc2d
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858726B2

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