Ethanol → HCID 131719201, compound

HRID 129111Notes

Reaction equation

HRID 129111 reaction equation
[C:1]([O:4][C@H:5]1[CH2:18][C@H:17]([O:19][C:20](=[O:22])[CH3:21])[C@@H:16]([CH3:23])[O:15][C@:6]1([NH:24][C:25](=[O:35])[CH2:26][P:27]([O:32][CH2:33][CH3:34])([O:29][CH2:30][CH3:31])=[O:28])[O:7]CC1C=CC=CC=1)(=[O:3])[CH3:2].C(O)C>[Pd].C(O)=O>[C:1]([O:4][C@H:5]1[CH2:18][C@H:17]([O:19][C:20](=[O:22])[CH3:21])[C@@H:16]([CH3:23])[O:15][C:6]1([NH:24][C:25](=[O:35])[CH2:26][P:27]([O:29][CH2:30][CH3:31])([O:32][CH2:33][CH3:34])=[O:28])[OH:7])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 22857244HCID 22857244, compound

Product 1

HCID 131719201HCID 131719201, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 284Formic AcidSolvent

Procedure

Crude benzyl 2,4-di-O-acetyl-3,6-dideoxydiethylphosphonoacetamido-alpha-D-mannopyranoside, 21, ethanol (10 mL), 2 88% formic acid and 0.1 g Pd black were heated at reflux overnight under argon with stirring. The reaction mixture was filtered and evaporated to dryness, and the residue was chromatographed on SiO2 (40 g; dichloromethane-methanol 95:5) to afford 0.57 g 2,4-di-O-acetyl-3,6-dideoxydiethylphosphonoacetamido-D-mannopyranose, as a yellow oil.

Workup

  1. temperatureat reflux overnight under argon
  2. filtrationThe reaction mixture was filtered
  3. customevaporated to dryness
  4. customthe residue was chromatographed on SiO2 (40 g; dichloromethane-methanol 95:5)

Sources & evidence

ORD record
ord-fb76325da33047068c58fc93ae1ae39f
Source dataset
uspto-grants-1995_11
Patent number
US05466809

Reaction notes

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