Triethylamine → HCID 12898206, compound

HRID 433868Notes

Reaction equation

HRID 433868 reaction equation
[C:1]([O:4][C@@H:5]1[O:22][C@H:21]([CH2:23]I)[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2].C(N(CC)CC)C.[H][H]>C(O)C.[Pd]>[C:1]([O:4][C@@H:5]1[O:22][C@H:21]([CH3:23])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13833585HCID 13833585, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12898206HCID 12898206, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1,2,3,4-Tetra-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranose (251.6 mg, 0.549 mmol) was dissolved in 20 mL of ethanol. To this solution was added 1 mL of triethylamine and 5% palladium on carbon (50.0 mg). The reaction mixture was exposed to 60 psi of hydrogen in a Parr apparatus at room temperature for 5 hours. The palladium on carbon was filtered off and the ethanol was removed in vacuo to yield a white solid. Purification via column chromatography over silica gel yielded 82.3 mg of the title compound as a white solid. (45%). MS(FAB) calculated for C14H20O9 (M+): 332.1. Found: 331.1.

Workup

  1. filtrationThe palladium on carbon was filtered off
  2. customthe ethanol was removed in vacuo
  3. customto yield a white solid
  4. customPurification via column chromatography over silica gel

Sources & evidence

ORD record
ord-44aa9575340e40838dab553fcc71d4cb
Source dataset
uspto-grants-2003_12
Patent number
US06670324B2

Reaction notes

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