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

HRID 2295339Notes

Reaction equation

HRID 2295339 reaction equation
I([O-])(=O)(=O)=O.I([O-])(=O)(=O)=O.[Na+].[CH2:12]([OH:15])[CH2:13][OH:14]>P([O-])([O-])([O-])=O.C(O)CC>[O:14]=[CH:13][C@@H:12]([C@H:13]([C@H:12]([C@@H:13]([CH2:12][OH:15])[OH:14])[OH:15])[OH:14])[OH:15]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 167232PeriodateHCID 23667635Sodium periodate

Product 1

HCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 1061PhosphateSolvent

Procedure

Periodate oxidations. The polysaccharide (0.3 mM galactose equivalents) was dissolved in phosphate buffer (20 ml) as before and 1-propanol (1 ml) was added followed by aqueous solutions (2 ml) of sodium metaperiodate (0.23 mM/mol hexose unit for guaran and 0.17 mM/mol hexose unit for locust bean gum). The oxidation was conducted at 5° C. in the dark for 15 hr after which it was stopped by addition of ethylene glycol (1 ml). When the oxidation was carried out in smaller solution volumes (~8 ml) the same ropy gels were obtained as in the case of galactose oxidase treatments. The dialdehyde products were isolated after dialysis (3 d).

Workup

  1. additionwas added
  2. customwas conducted at 5° C.
  3. customdark for 15 hr

Sources & evidence

ORD record
ord-a41d845836254f3ca1ccea71fb3d6d72
Source dataset
uspto-grants-1984_01
Patent number
US04424346

Reaction notes

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