Acetic Anhydride → GlyTouCan:G72770YD

HRID 560964Notes

Reaction equation

HRID 560964 reaction equation
[N:1]([C@H:4]1[C@@H:17]([OH:18])[C@H:16]([F:19])[C@@H:15]([CH2:20][OH:21])[O:14][C@H:5]1[O:6]CC1C=CC=CC=1)=[N+]=[N-].[C:22](OC(=O)C)(=[O:24])[CH3:23].[H][H]>CO.[Pd]>[C:22]([NH:1][C@H:4]1[C@@H:17]([OH:18])[C@H:16]([F:19])[C@@H:15]([CH2:20][OH:21])[O:14][CH:5]1[OH:6])(=[O:24])[CH3:23]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 86600946benzyl 2-azido-2,4-dideoxy-4-fluoro-beta-D-mannopyranosideHCID 178418361HCID 178418361, compound

Product 1

HCID 86600945GlyTouCan:G72770YD

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound (23) (105 mg, 0.353 mmol) was dissolved in methanol (7 ml), acetic anhydride (333 μl, 3.53 mols) was added to the solution, a catalytic amount of 10% Pd/C was thereafter added to the mixture, and the resulting mixture was stirred at room temperature after replacing the atmosphere in the reactor with hydrogen. TLC indicated disappearance of the material 2 hours later, followed by filtration with activated carbon and concentration. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=5:1), giving Compound (24) (in an amount of 57 mg, 72% in yield).

Workup

  1. customdisappearance of the material 2 hours
  2. filtrationfollowed by filtration with activated carbon and concentration
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=5:1)

Sources & evidence

ORD record
ord-c279c8b3f75545319d8008593b477243
Source dataset
uspto-grants-2011_11
Patent number
US08063202B2

Reaction notes

Loading…