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

HRID 25470

Reaction equation

HRID 25470 reaction equation
[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.CS(C)=O.C(OC(=O)C)(=O)C>>[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

Participants

3

Reactant 2

HCID 7067560Diacetone-D-glucoseHCID 86609981DMSO acetic anhydride

Product 1

HCID 71570541,2:5,6-Bis-O-(1-methylethylidene)-alpha-D-allofuranoseYield 58%

Procedure

The surprising finding according the present invention is that it is possible to carry out the oxidation of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose with DMSO/acetic anhydride in one pot with the subsequent reduction of the 1,2:5,6-di-O-isopropylidene-α-D-ribofuranose-3-ulose to form 1,2:5,6-di-O-isopropylidene-α-D-allofuranose (formula I). It is very surprising that the reduction can be carried out in the presence of the oxidation mixture. It is also surprising that it is possible to use this oxidation procedure in large scale (1 mole), and that the lowest reported amount of excess acetic anhydride (5 times) provides 58 % yield of recrystallised and analytical pure 1,2:5,6-di-O-isopropylidene-α-D-allofuranose.

Sources & evidence

ORD record
ord-70af49f9fb64449f8c4213e49877ea46
Source dataset
uspto-grants-2005_02
Patent number
US06858726B2

Linked notes

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