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

HRID 905316Notes

Reaction equation

HRID 905316 reaction equation
C1(NC2C=CC=CC=2)C=CC=CC=1.NC1C=CC=CC=1.P(=O)(O)(O)O.C(OCC)(=O)C.[O:32]=[CH:33][C@@H:34]([C@H:36]([C@@H:38]([C@@H:40]([CH2:42][OH:43])[OH:41])[OH:39])[OH:37])[OH:35]>>[CH2:42]([OH:43])[C@@H:40]([OH:41])[C@@H:38]([OH:39])[C@H:36]([OH:37])[C:34]([CH:33]=[O:32])=[O:35]

Participants

3

Reactant 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 86737447Diphenylamine aniline phosphoric acid ethyl acetate

Product 1

HCID 159630D-Glucosone

Conditions

Temperature
100 °C

Procedure

Thin layer chromatography (TLC)--Avicel coated glass plates are developed with an 8:8:2:4 (by volume); isopropanol:pyridine:acetic acid:water solvent system. Glucose has Rf 's 0.5-0.6; D-glucosone has an Rf 0.4-0.5 streak. (Rf =the distance substance migrates from origin/solvent front distance from origin). When the plates are sprayed with triphenyltetrazolium chloride (2% TTC in 0.5 N NaOH), D-glucosone instantly yields a red spot; glucose yields a red spot only upon heating for ten minutes at 100° C. When the plates are sprayed with diphenylamine/aniline/phosphoric acid/ethyl acetate reagent, (0.15 g/0.8 ml/11 ml/100 ml), glucose yields a brown spot; D-glucosone yields a purple streak upon heating for 10 minutes at 95° C.

Workup

  1. customyields a brown spot

Sources & evidence

ORD record
ord-debce6f3a07b4733a993e98891786b9a
Source dataset
uspto-grants-1983_12
Patent number
US04423149

Reaction notes

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