Water → HCID 86660599, compound

HRID 2367952Notes

Reaction equation

HRID 2367952 reaction equation
C([C:4]([C@H:6]([C@@H:8]([C@@H:10]([N:13]=[N+:14]=[N-:15])[CH2:11][OH:12])[OH:9])[OH:7])=[O:5])C=C.O>CO.[Pd](Cl)Cl>[N:13]([C@@H:10]([CH2:11][OH:12])[C@@H:8]([OH:9])[C@H:6]([OH:7])[CH:4]=[O:5])=[N+:14]=[N-:15]

Participants

5

Reactant 2

HCID 962WaterHCID 86660597HCID 86660597, compound

Product 1

HCID 86660599HCID 86660599, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 887MethanolSolvent

Procedure

1-allyl-4-azido-4-deoxy-L-xylose 36 (496 mg, 2.3 mmol) was dissolved in 99:1 methanol:water (10 mL), followed by the addition of palladium (II) chloride (81.7 mg, 0.46 mmol). The reaction mixture was stirred for 24 h at room temperature, and then filtered through a pad of Celite® with methanol wash (100 mL). The combined filtrates were purified by silica gel flash chromatography (DCM to 9:1 DCM:MeOH) to give of 37 as a yellow oil (249 mg, 1.42 mmol, 62%).

Workup

  1. filtrationfiltered through a pad of Celite® with methanol
  2. washwash (100 mL)
  3. customThe combined filtrates were purified by silica gel flash chromatography (DCM to 9:1 DCM:MeOH)

Sources & evidence

ORD record
ord-a85fe197dcb04456919ae645c4e0913e
Source dataset
uspto-grants-2014_04
Patent number
US08703723B2

Reaction notes

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