Pyridine → Methyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-beta-D-glucopyranoside

HRID 2372162Notes

Reaction equation

HRID 2372162 reaction equation
N1C=CC=CC=1.[F:7][C:8]([F:21])([F:20])[S:9]([O:12]S(C(F)(F)F)(=O)=O)(=[O:11])=[O:10].[CH2:22]([O:29][C@@H:30]1[C@@H:37]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C@H:36]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@@H:35]([CH2:54]O)[O:34][C@H:31]1[O:32][CH3:33])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([O:29][C@@H:30]1[C@@H:37]([O:38][CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C@H:36]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@@H:35]([CH2:54][O:12][S:9]([C:8]([F:21])([F:20])[F:7])(=[O:11])=[O:10])[O:34][C@H:31]1[O:32][CH3:33])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 11113352methyl 2,3,4-tri-O-benzyl-beta-D-glucopyranoside

Product 1

HCID 22842886Methyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-beta-D-glucopyranosideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a solution of dry pyridine (0.456 mL) in methylene chloride (20 mL) cooled to -15° C. was added trifluoromethanesulfonic anhydride (0.864 mL). The mixture was stirred during 15 min at -10° C., then methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside (1.2 g, 2.58 mmol) in methylene chloride (30 mL) was added [P. Kovac, J. Alfoldi and M. Kosik, Chem. Zvesti 28, 820, (1974)]. The mixture was stirred during 1.5 h at -10° C. The reaction mixture was washed with water. 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 7:2 mixture of hexane and ethyl acetate afforded the expected compound methyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl -β-D-glucopyranoside (1.408 g, 89%) as an oil, which crystallized in the fridge.

Workup

  1. stirringThe mixture was stirred during 1.5 h at -10° C
  2. washThe reaction mixture was washed with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford an oil
  7. washFlash chromatography on silica gel and elution
  8. additionwith a 7:2 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-c8dd54ea4d554afeb5657d70f05e8a4b
Source dataset
uspto-grants-1992_03
Patent number
US05097023

Reaction notes

Loading…