Acetic Acid → HCID 69398687, compound

HRID 860840Notes

Reaction equation

HRID 860840 reaction equation
O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[NH:13]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC(O)=O>CCO>[CH2:21]([N:13]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:2][C:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])=[O:4])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7656DibenzylamineHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 69398687HCID 69398687, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of D-glucose (36.0 g, 200.0 mmol) and Bn2NH (39.5 g, 200.0 mmol) in absolute EtOH (200 mL) was added AcOH (12.0 g, 200.0 mmol). Upon refluxing for 3 h, the reaction mixture was cooled and filtered with suction. The resulting filter cake was washed with EtOH to colorless and dried in a desiccator over calcium chloride to give 1-dibenzylamino-1-deoxy-D-fructose as a white solid (57.0 g, 79%).

Workup

  1. temperatureUpon refluxing for 3 h
  2. temperaturethe reaction mixture was cooled
  3. filtrationfiltered with suction
  4. filtrationThe resulting filter cake
  5. washwas washed with EtOH to colorless and
  6. dry with materialdried in a desiccator over calcium chloride

Sources & evidence

ORD record
ord-22b87320c78843fdb5e1c3d7944ae0af
Source dataset
uspto-grants-2006_12
Patent number
US07153971B2

Reaction notes

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