Trifluoroacetic acid → HCID 86642459, compound

HRID 2068490Notes

Reaction equation

HRID 2068490 reaction equation
[I:1][C@@H:2]1[C@@H:15]([OH:16])[C@H:14]([OH:17])[C@@H:13]([CH2:18][OH:19])[O:12][C@H:3]1[O:4][Si](CC)(CC)CC.C1COCC1.FC(F)(F)C(O)=O>O>[I:1][C@H:2]([C@H:15]([C@@H:14]([C@@H:13]([CH2:18][OH:19])[OH:12])[OH:17])[OH:16])[CH:3]=[O:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 86642454HCID 86642454, compound

Product 1

HCID 86642459HCID 86642459, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Mixture of 2-deoxy-2-iodo-1-O-triethylsilyl-β-D-glucopyranose (VI) (0.1 g), THF (2 mL), water (0.5 mL) and trifluoroacetic acid (0.1 mL) was prepared and stirred at room temperature. Progress of the reaction was monitored by TLC and after substrate disappearance reaction mixture was washed with dichloromethane (5×10 mL). The remaining water solution was lyophilized and such obtained crude solid residue was purified by column chromatography (SilicaGel 60, Merck) using chloroform, chloroform:methanol 9:1, 7:3 as eluents, to give (0.05 g) of 2-deoxy-2-iodo-D-glucose (VII). Yield 70%.

Workup

  1. customwas prepared
  2. customafter substrate disappearance reaction mixture
  3. washwas washed with dichloromethane (5×10 mL)
  4. customsuch obtained crude solid residue
  5. customwas purified by column chromatography (SilicaGel 60, Merck)

Sources & evidence

ORD record
ord-d9508b4c92a747fc81b365ed547278ee
Source dataset
uspto-grants-2012_10
Patent number
US08299033B2

Reaction notes

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