HCID 11167178, compound → HCID 54028878, compound

HRID 2372155Notes

Reaction equation

HRID 2372155 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:15]([OH:25])[C@@H:14]([CH2:26][O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:13][C@@H:10]1[O:11]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O.O>[CH2:1]([O:8][C@@H:9]1[C@@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:15]([OH:25])[C@@H:14]([CH2:26][O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:13][CH:10]1[OH:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 11167178HCID 11167178, compound

Product 1

HCID 54028878HCID 54028878, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside (5 g, 10.775 mmol) was dissolved at 0° C. in a 9:1 mixture of trifluoroacetic acid and water (50 mL) [N. Morishima, S. Koto, M. Oshima, A. Sugimoto and S. Zen, Bull Chem. Soc. Jpn 56, 2849 (1983)]. The mixture was stirred overnight at 0° C. The solvents were evaporated under reduced pressure without heating. The residue was dissolved in ethyl acetate and washed successively with sodium bi-carbonate and brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford an oil. Flash chromatography on silica gel and elution with a graded mixture of ethyl acetate and hexane afforded 2,3,6-tri-O-benzyl-D-galactopyranose (3.927 g, 81%) as an oil.

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. temperaturewithout heating
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed successively with sodium bi-carbonate and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford an oil
  9. washFlash chromatography on silica gel and elution
  10. additionwith a graded mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-83340f425a4a46d7bd2af2a13dfa200c
Source dataset
uspto-grants-1992_03
Patent number
US05097023

Reaction notes

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