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

HRID 426971Notes

Reaction equation

HRID 426971 reaction equation
C(B1[O:7][CH2:6][CH2:5][O:4]1)C.[CH2:8]([OH:11])[CH2:9][OH:10]>>[O:10]=[CH:9][C@@H:8]([C@H:5]([C@@H:6]([C@@H:6]([CH2:5][OH:4])[OH:7])[OH:7])[OH:4])[OH:11]

Participants

3

Reactant 2

HCID 174Ethylene GlycolHCID 250302-Ethyl-1,3,2-dioxaborolane

Product 1

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalYield 72%

Procedure

20 ml of ethane-1,2-diol are added dropwise at 50° C. to 11 g of residue and at the same time the 2-ethyl-1,3,2-dioxaborolane formed is distilled off in vacuo (10 Torr). The excess ethane-1,2-diol is removed in vacuo (10-3Torr, bath 80° C.). Approximately 40 ml of hexane are added to the highly viscous residue, the mixture is stirred for about 30 minutes and the white glucose is filtered off. 5 g (72%) of pure D-glucose are obtained after drying, mp. 146° C.

Workup

  1. customformed
  2. distillationis distilled off in vacuo (10 Torr)
  3. customThe excess ethane-1,2-diol is removed in vacuo (10-3Torr, bath 80° C.)
  4. additionApproximately 40 ml of hexane are added to the highly viscous residue
  5. filtrationthe white glucose is filtered off

Sources & evidence

ORD record
ord-f689c640c3374f2ba71ad244f9df165d
Source dataset
uspto-grants-1979_10
Patent number
US04172195

Reaction notes

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