(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → Diacetone-D-glucose

HRID 2051673Notes

Reaction equation

HRID 2051673 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4]>CC(C)=O>[CH3:2][C:3]1([CH3:5])[O:4][C@@H:3]([C@H:5]2[O:6][C@@H:11]3[O:12][C:9]([CH3:11])([CH3:7])[O:10][C@@H:9]3[C@H:7]2[OH:8])[CH2:2][O:1]1

Participants

3

Reactant 1

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 7067560Diacetone-D-glucose

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The process of claim 1 where the 1,2:5,6-di-O-isopropylidene-3-amino-3-deoxy-α-D-allofuranose is prepared by reacting D-glucose with acetone to produce 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, oxidizing the glucofuranose to produce 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranose-3-ulose, subjecting the hexofuranose to oximization to produce 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranose-3-ulose oxime, and reducing the oxime to produce said 1,2:5,6-di-O-isopropylidene-3-amino-3-deoxy-α-D-allofuranose.

Sources & evidence

ORD record
ord-e87a757fe42c4697bd60f6f8529da7d5
Source dataset
uspto-grants-1980_01
Patent number
US04181795

Reaction notes

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