Hydrazine, acetate (1:1) → HCID 21310460, compound

HRID 583159Notes

Reaction equation

HRID 583159 reaction equation
C([C:4]1([O:26][C@H:25]([CH2:27][O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:6]1[F:36])[OH:5])(=O)C.C(O)(=O)C.NN>CN(C=O)C.ClCCl>[F:36][C@@H:6]1[C@@H:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C@H:16]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C@@H:25]([CH2:27][O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:26][CH:4]1[OH:5]

Participants

5

Reactant 2

HCID 165591Hydrazine, acetate (1:1)HCID 131721315HCID 131721315, compound

Product 1

HCID 21310460HCID 21310460, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Acetyl-2-deoxy-2-fluoro-3,4,6-tri-O-benzyl-glucopyranose (750 mg) was dissolved in anhydrous DMF (7.5 mL). Hydrazine acetate (300 mg) was added and the reaction mixture was stirred for 3 hours at room temperature until most of the starting material was converted into product. The solution was diluted with dichloromethane (150 mL) and the organic layer was washed with water (3×150 mL), dried over sodium sulfate, filtered and evaporated. Chromatography of the material on silica gel using hexane-ethyl acetate (5:1) as eluent provided 2-deoxy-2-fluoro-3,4,6-tri-O-benzyl glucopyranose (500 mg).

Workup

  1. washthe organic layer was washed with water (3×150 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-27009157a6af4126ab4a59bbdf4c2867
Source dataset
uspto-grants-1999_07
Patent number
US05929037

Reaction notes

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