Hydrazine, acetate (1:1) → HCID 10641435, compound

HRID 1985998Notes

Reaction equation

HRID 1985998 reaction equation
C([O:4][C@H:5]1[O:22][C@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.C(O)(=O)C.NN>CN(C=O)C>[C:8]([O:7][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:22][C@@H:5]1[OH:4])(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 165591Hydrazine, acetate (1:1)HCID 2723636alpha-D-Glucopyranosyl pentaacetate

Product 1

HCID 10641435HCID 10641435, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 80 ml of DMF was dissolved 5.18 g of α-D-glucose pentaacetate, and 2.37 g of hydrazine acetate was added thereto, followed by stirring at room temperature for 1.5 hours. The reaction mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure to obtain 4.0 g of α-D-glucopyranose-2,3,4,6-tetraacetate (yield: 87%).

Workup

  1. additionwas added
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe ethyl acetate layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate
  5. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2d99489af1814cfb9658879f2b19d318
Source dataset
uspto-grants-2009_06
Patent number
US07547765B2

Reaction notes

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