Acetic Acid → HCID 67930744, compound

HRID 728214Notes

Reaction equation

HRID 728214 reaction equation
[CH2:1]1[O:8][C@@H:7]2[O:9][C@H:2]1[CH:3]=[CH:4][C:5]2=[O:6].[K].[BH4-].[Na+].[C:13]([OH:16])(=O)[CH3:14]>C(O)C1C=CC=CC=1.C(O)C>[CH2:13]([O:16][C@@H:3]1[C@H:2]2[CH2:1][O:8][C@H:7]([O:9]2)[C:5](=[O:6])[CH2:4]1)[C:14]1[CH:5]=[CH:4][CH:3]=[CH:2][CH:1]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 699486LevoglucosenoneHCID 4311764Sodium borohydrideHCID 5462222Potassium

Product 1

HCID 67930744HCID 67930744, compound

Reagents, catalysts & solvents 2

HCID 244Benzyl AlcoholSolventHCID 702EthanolSolvent

Procedure

A solution of 1,6-anhydro-4-O-benzyl-3-deoxy-β-D-erythro-hexopyranos-2-ulose in benzyl alcohol was prepared as described in Example 6, except that 0.088 g of levoglucosenone were used as starting material and, 5 min after the addition of potassium benzoxide, a suspension of sodium borohydride (0.073 g) in ethanol (4 ml) was added to the mixture, which was then stirred for 0.5 h at room temperature, made neutral with acetic acid, evaporated under vacuum, and the resulting white residue transferred to a short column of silica, which was eluted with a gradient of ethyl acetate/hexane (from 1:2 to 2:1). The fractions found by t.l.c. to contain the title compound A were combined and evaporated, to give material that spontaneously crystallized (0.106 g, 64% from levoglucosenone). 1H-Nmr spectroscopy of this material showed it to be an 9:11 mixture of the title compound A and the D-arabino isomer determined from the relative intensities of their H-3 resonances.

Workup

  1. custommaterial and, 5 min
  2. additionwas added to the mixture, which
  3. customevaporated under vacuum
  4. washwas eluted with a gradient of ethyl acetate/hexane (from 1:2 to 2:1)
  5. customevaporated
  6. customto give material that
  7. customspontaneously crystallized (0.106 g, 64% from levoglucosenone)
  8. additionan 9:11 mixture of the title compound A

Sources & evidence

ORD record
ord-731674a9cf704351a1fbff682da8b719
Source dataset
uspto-grants-1991_09
Patent number
US05047518

Reaction notes

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