Potassium → HCID 66980194, compound

HRID 1508418Notes

Reaction equation

HRID 1508418 reaction equation
[K].[CH2:2]([O:4][C:5](=[O:18])/[C:6](/[O-:17])=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])[CH3:3].[K+].[C:20]([O:23][C@@H:24]1[C@@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@@H:29]([O:35][C:36](=[O:38])[CH3:37])[C@@H:28]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[O:27][C@@H:25]1O)(=[O:22])[CH3:21]>CN(C=O)C>[C:36]([O:35][C@H:29]1[C@@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@H:24]([O:23][C:20](=[O:22])[CH3:21])[C@@H:25]([O:17]/[C:6](/[C:5]([O:4][CH2:2][CH3:3])=[O:18])=[CH:7]\[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[O:27][C@H:28]1[CH2:39][O:40][C:41](=[O:43])[CH3:42])(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 5462222PotassiumHCID 11013484[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-hydroxyoxan-2-yl]methyl acetateHCID 13466187HCID 13466187, compound

Product 1

HCID 66980194HCID 66980194, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The solution of potassium salt of 2-nitrophenylpyruvate B2 (100 mg, 0.36 mmol) in dry DMF (3 mL) was added dropwise over a period of 15 min, to a pre-cooled stirred solution of 2,3,4,6-tetra-O-acetyl-α-D-galactose (149 mg, 0.36 mmol) in dry DMF (2 mL) at 0° C. under nitrogen atmosphere. The temperature was gradually raised to room temperature. Reaction mixture was allowed to stir for 15 h, and the reaction was quenched with chilled, saturated aq. NaCl (25 mL). Extraction with ethyl acetate (3×30 mL), drying (MgSO4), concentration under reduced pressure, and purification by flash chromatography (SiO2, hexane-benzene-acetone-methanol, 5:4:5:1) to isolate the pure resultant compound C3 in 50% yield.

Workup

  1. customReaction mixture
  2. customthe reaction was quenched
  3. temperaturewith chilled
  4. extractionExtraction with ethyl acetate (3×30 mL)
  5. customdrying
  6. concentration(MgSO4), concentration
  7. customunder reduced pressure, and purification by flash chromatography (SiO2, hexane-benzene-acetone-methanol, 5:4:5:1)

Sources & evidence

ORD record
ord-69febd4a965244609d16845698554d11
Source dataset
uspto-grants-2015_12
Patent number
US09221860B2

Reaction notes

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