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

HRID 1450675Notes

Reaction equation

HRID 1450675 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)C=O>[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 61.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 g (25.6 mmoles) of α-D-glucose pentaacetate and 2 g (21.7 mmoles) of hydrazine acetate in N,N-dimethylformamide were together stirred at 50° C. for 45 minutes. The reaction solution was extracted with ethyl acetate, and washed with a saturated aqueous sodium chloride solution. After working up in a conventional manner, purification by silica gel column chromatography (eluent; ether: n-hexane =2:1 to 3:1) gave 5.45 g of 2,3,4,6-tetra-O-acetyl-α-D-glucose.

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washwashed with a saturated aqueous sodium chloride solution
  3. customAfter working up in a conventional manner, purification by silica gel column chromatography (eluent; ether: n-hexane =2:1 to 3:1)

Sources & evidence

ORD record
ord-bac8bcd551dc41d4bf95e4e877a664c1
Source dataset
uspto-grants-1997_02
Patent number
US05602239

Reaction notes

Loading…