(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → (3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one

HRID 1826568Notes

Reaction equation

HRID 1826568 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]>C(O)C>[OH:1][CH2:2][C:3]([C@H:5]([C@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])=[O:4]

Participants

3

Reactant 1

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

Product 1

HCID 92092(3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

U.S. Pat. No. 6,057,135 discloses a process for manufacturing D-tagatose, wherein a lactose permeate is hydrolysed to obtain a lactose hydrolysate comprising D-galactose and glucose. The hydrolysate is fermented to convert the glucose to ethanol which is subsequently removed and the remaining solution of D-galactose is subjected to enzymatic isomerisation with an L-arabinose isomerase to obtain D-tagatose. The L-arabinose isomerase preparations used are crude biomass extracts of Lactobacillus pentosus, Bacillus amyloliquefaciens or Arthrobacter spp

Workup

  1. customis subsequently removed

Sources & evidence

ORD record
ord-661fddfc49ce48af948521822a6e48db
Source dataset
uspto-grants-2006_05
Patent number
US07052898B2

Reaction notes

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