HCID 11167178, compound → HCID 54028878, compound

HRID 1720178Notes

Reaction equation

HRID 1720178 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, compound

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) is 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. is stirred overnight at 0° C. The solvents are evaporated under reduced pressure without heating. The residue is dissolved in ethyl acetate and washed successively with sodium bicarbonate and brine. The organic layer is dried over sodium sulfate, filtered and concentrated under reduced pressure so as to afford an oil. Flash chromatography on silica gel and elution with a graded mixture of ethyl acetate and hexane will afford 2,3,6-tri-O-benzyl-D-galactopyranose as an oil.

Workup

  1. customThe solvents are evaporated under reduced pressure
  2. temperaturewithout heating
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed successively with sodium bicarbonate and brine
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure so as
  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-6cc86874b4904220905d88c0ca7c4af1
Source dataset
uspto-grants-1996_04
Patent number
US05504078

Reaction notes

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