Potassium Carbonate → HCID 86642454, compound

HRID 2068488Notes

Reaction equation

HRID 2068488 reaction equation
[I:1][C@@H:2]1[C@@H:15]([O:16]C(=O)C)[C@H:14]([O:20]C(=O)C)[C@@H:13]([CH2:24][O:25]C(=O)C)[O:12][C@H:3]1[O:4][Si:5]([CH2:10][CH3:11])([CH2:8][CH3:9])[CH2:6][CH3:7].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.CO>[I:1][C@@H:2]1[C@@H:15]([OH:16])[C@H:14]([OH:20])[C@@H:13]([CH2:24][OH:25])[O:12][C@H:3]1[O:4][Si:5]([CH2:10][CH3:11])([CH2:6][CH3:7])[CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86642455HCID 86642455, compound

Product 1

HCID 86642454HCID 86642454, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Subsequently, the 2-deoxy-2-iodo-3,4,6-tri-O-acetyl-1-O-triethylsilyl-β-D-glucopyranose (III) (0.7 g) was dissolved in the mixture of chloroform:methanol (7:3 v/v) (15 mL). Potassium carbonate (4 g) was added, and reaction mixture was stirred at room temperature until substrate deacetylation has been completed. Inorganic salts were filtered off and solvents were evaporated. Such obtained product was purified by column chromatography (SilicaGel 60, Merck) using chloroform and chloroform:methanol 99:1 as eluents, to give (0.1 g) of 2-deoxy-2-iodo-1-O-triethylsilyl-β-D-glucopyranose (VI) (yield 20%).

Workup

  1. customreaction mixture
  2. filtrationInorganic salts were filtered off
  3. customsolvents were evaporated
  4. customSuch obtained product was purified by column chromatography (SilicaGel 60, Merck)

Sources & evidence

ORD record
ord-c8ab18b5781f4c8aa5d414179b69e019
Source dataset
uspto-grants-2012_10
Patent number
US08299033B2

Reaction notes

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