Glyoxal → delta-Gluconolactone

HRID 46212

Reaction equation

HRID 46212 reaction equation
ClC1C=CC([C@H:8]2[C@H:13]([O:14]CC3C=CC=CC=3)[C@@H:12]([O:22]CC3C=CC=CC=3)[C@H:11]([O:30]CC3C=CC=CC=3)[C@@H:10]([CH2:38][O:39]CC3C=CC=CC=3)[O:9]2)=CC=1CC(=N)NN.C(C=O)=[O:53]>CCO>[CH2:38]([OH:39])[C@H:10]1[O:9][C:8](=[O:53])[C@H:13]([OH:14])[C@@H:12]([OH:22])[C@@H:11]1[OH:30]

Participants

4

Reactant 2

HCID 7860GlyoxalHCID 178510822HCID 178510822, compound2×

Product 1

HCID 7027delta-GluconolactoneYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)acetimidohydrazide (compound 45, crude 1 g from step 1) in EtOH (30 ml) reacted with glyoxal (5 ml, 30% in water) at 0° C., and allowed to warm up at room temperature. After the reaction mixture was stirred for 3 hours, it was evaporated under reduced pressure to remove volatile compounds. The residue was purified with silica gel (Hx/EtOAc=⅓) to provided title compound (324 mg, 60% overall yield form intermediate 2).

Workup

  1. customit was evaporated under reduced pressure
  2. customto remove volatile compounds
  3. customThe residue was purified with silica gel (Hx/EtOAc=⅓)

Sources & evidence

ORD record
ord-dccbd57b1b6343c194f85b8bf62d9678
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Linked notes

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