Triethylamine → allyl-3-O-methyl-glucopyranose

HRID 583163Notes

Reaction equation

HRID 583163 reaction equation
[CH3:1][O:2][C@H:3]1[C@H:9]([OH:10])[C@@H:8]([CH2:11][OH:12])[O:7][CH:5]([OH:6])[C@@H:4]1[OH:13].F[C:15](F)(F)S(O)(=O)=O.C(N([CH2:27][CH3:28])CC)C>FC(F)(F)C(O)=O.C(O)C=C>[CH2:15]([C:5]1([O:7][C@H:8]([CH2:11][OH:12])[C@@H:9]([OH:10])[C@H:3]([O:2][CH3:1])[C@H:4]1[OH:13])[OH:6])[CH:27]=[CH2:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62406Trifluoromethanesulfonic acidHCID 96241D-Glucoyranose, 3-O-methyl-

Product 1

HCID 131720021allyl-3-O-methyl-glucopyranoseYield 50.8%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7858Allyl AlcoholSolvent

Procedure

3-O-methyl-1,2:5,6-di-O-isopropylidine-glucopyranose (10.2 g) was dissolved in 90% aqueous trifluoroacetic acid (30 mL) and stirred for 1 hour at room temperature. The reaction mixture was evaporated and then coevaporated with toluene followed by ethanol coevaporation to provide the product which was directly used for further allyl glycosylation. 7.9 g of 3-O-methyl-glucopyranose was dissolved in 50 mL of dry allyl alcohol and 120 μL of trifluoromethanesulfonic acid was added. The mixture was heated for 51/2 h at 80° C. Triethylamine (1 mL) was added to destroy excess trifluoromethanesulfonic acid, evaporated and coevaporated with water to remove allyl alcohol. The material was purified by chromatography on silica gel using dichloromethane-methanol (20:1) as eluent to yield allyl-3-O-methyl-glucopyranose (4.85 g, 50.8%).

Workup

  1. customThe reaction mixture was evaporated
  2. customto provide the product which
  3. temperatureThe mixture was heated for 51/2 h at 80° C
  4. customto destroy excess trifluoromethanesulfonic acid
  5. customevaporated
  6. customto remove allyl alcohol
  7. customThe material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-301f63b157184e28b42b7d953e67a4ef
Source dataset
uspto-grants-1999_07
Patent number
US05929037

Reaction notes

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