HCID 53871764, compound → HCID 10649365, compound

HRID 1757076Notes

Reaction equation

HRID 1757076 reaction equation
[C@H:1]1([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:20]=[C:21]([CH2:25][CH:26]=[CH:27][P:28](=[O:35])([O:32][CH2:33][CH3:34])[O:29][CH2:30][CH3:31])[CH:22]=[CH:23][CH:24]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:2]1[OH:3]>C(O)C.[Pd]>[C@H:1]1([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:20]=[C:21]([CH2:25][CH2:26][CH2:27][P:28](=[O:35])([O:29][CH2:30][CH3:31])[O:32][CH2:33][CH3:34])[CH:22]=[CH:23][CH:24]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:2]1[OH:3]

Participants

4

Reactant 1

HCID 53871764HCID 53871764, compound

Product 1

HCID 10649365HCID 10649365, compoundYield 112.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Diethyl 3-(3-(2-α-D-mannopyranosyloxyphenyl)phenyl)prop-1-enylphosphonate (0.46 g, 0.80 mmol) was dissolved in ethanol (25 ml) and hydrogenated (40 psi H2, 10% Pd/C) for 3 hours. The suspension was filtered through celite and the filtrate concentrated under reduced pressure to afford diethyl 3-(3-(2-α-D-mannopyranosyloxyphenyl)phenyl)propylphosphonate (0.46 g, quantitative).

Workup

  1. filtrationThe suspension was filtered through celite
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-14e4a4a21b9c41a5822c4c0441416ed8
Source dataset
uspto-grants-1995_08
Patent number
US05444050

Reaction notes

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