Acetic Anhydride → 4-acetamidophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 6050

Reaction equation

HRID 6050 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:18][S:17][C@H:6]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)(=[O:3])[CH3:2].[C:29](OC(=O)C)(=[O:31])[CH3:30]>[Pd]>[C:1]([O:4][C@@H:5]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:18][S:17][C@H:6]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:29](=[O:31])[CH3:30])=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 150678484-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Product 1

HCID 150678624-acetamidophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranosideYield 51%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

30 mg of 10% palladium-on-charcoal are added to a solution of 150 mg (0.36.10-3 mol) of 4-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside in acetic anhydride, under a nitrogen atmosphere, and the reaction mixture obtained is then kept under hydrogen pressure (3.5.105Pa) at 50° C. for 15 hours. After filtration, the mixture is evaporated to dryness under reduced pressure and the residue obtained is purified by chromatography using a methylene chloride/methanol mixture (98/2 v/v) as the eluent to give 80 mg (yield: 51%) of the expected product.

Workup

  1. customthe reaction mixture obtained
  2. customat 50° C.
  3. customfor 15 hours
  4. filtrationAfter filtration
  5. customthe mixture is evaporated to dryness under reduced pressure
  6. customthe residue obtained
  7. customis purified by chromatography

Sources & evidence

ORD record
ord-a861c83a05a249d8b29e8cc1b67b61a7
Source dataset
uspto-grants-1993_09
Patent number
US05246961

Linked notes

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