D-xylo-5-Hexulosonic acid → D-Arabinose

HRID 2182075Notes

Reaction equation

HRID 2182075 reaction equation
C(O)[C:2]([C@@H:4]([OH:12])[C@H:5]([OH:11])[C@@H:6]([OH:10])[C:7](O)=[O:8])=[O:3].[H][H]>[Ni]>[O:3]=[CH:2][C@H:4]([C@@H:5]([C@H:6]([CH2:7][OH:8])[OH:10])[OH:11])[OH:12].[O:3]=[CH:2][C@H:4]([C@@H:5]([C@@H:6]([CH2:7][OH:8])[OH:10])[OH:11])[OH:12]

Participants

5

Reactant 2

HCID 5460352D-xylo-5-Hexulosonic acidHCID 178418361HCID 178418361, compound

Product 2

HCID 66308D-ArabinoseHCID 95259L-Xylose

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Hydrogenation of 5-keto-D-gluconic acid to D-gluconic- and L-idonic acids was performed under the following conditions: Hydrogen pressure was 40 bar, reaction temperature 100° C. pH of the feed was adjusted to 5 before reaction. Feed syrup concentration was 400 g/l. The catalyst was Raney-nickel and the catalyst load was 10% wet catalyst per feed dry substance. Decarboxylation of the obtained mixture of D-gluconic acid and L-idonic acid as described in examples 5 and 6 yields L-xylose and D-arabinose, which subsequently are separated by chromatography.

Workup

  1. custom40 bar, reaction temperature 100° C. pH of the feed
  2. customwas adjusted to 5 before reaction
  3. customdry substance
  4. additionDecarboxylation of the obtained mixture of D-gluconic acid and L-idonic acid

Sources & evidence

ORD record
ord-98b80be374e64be181dbbbab9c1cef28
Source dataset
uspto-grants-2005_05
Patent number
US06894199B2

Reaction notes

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