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

HRID 622065Notes

Reaction equation

HRID 622065 reaction equation
[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].[CH2:7]([OH:14])[C@@H:8]([C@@H:10](CO)[OH:11])[OH:9]>S(=O)(=O)(O)O>[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:8]([CH2:10][OH:11])[OH:9])[OH:14])[OH:6])[OH:4]

Participants

4

Reactant 2

HCID 753GlycerolHCID 222285Erythritol

Product 1

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

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Separately, the polyol-type ganoderan was kept at 90°-100° C. for 1-2 hours in 0.05-0.1M sulfuric acid to obtain, as well as glycerol and erythritol, an insoluble substance. Hydrolysis of the insoluble substance gave D-glucose as sole product, while hydrolysis of a methylated polyol-type ganoderan gave a substantial amount of 2,4,6-tri-O-methyl-D-glucose. By exposure to the action of exo-beta-1,3 glucanase, only D-glucose was obtained. These facts confirm that the backbone of ganoderan consists of beta-1,3-linked D-glucopyranose residues.

Workup

  1. customto obtain
  2. customHydrolysis of the insoluble substance

Sources & evidence

ORD record
ord-79b1917a9c6a4120a5e74642eee839ec
Source dataset
uspto-grants-1988_09
Patent number
US04769363

Reaction notes

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