Sodium Bicarbonate → tetrahydro-2H-pyran-2-yl 2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranose

HRID 1641519Notes

Reaction equation

HRID 1641519 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[S:8][CH:6]1[OH:7])(=[O:3])[CH3:2].O.[C:26]1(C)C=[CH:30][C:29](S(O)(=O)=O)=[CH:28][CH:27]=1.C(=O)(O)[O-:38].[Na+]>C(Cl)(Cl)Cl.O1C=CCCC1>[O:38]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[C:6]1([S:8][C@H:9]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[C@@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:5]1[O:4][C:1](=[O:3])[CH3:2])[OH:7]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 116462702,3,4,6-tetra-O-acetyl-5-thio-glucopyranose

Product 1

HCID 131728755tetrahydro-2H-pyran-2-yl 2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranose

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 80803,4-dihydro-2H-pyranSolvent

Procedure

To a solution of 2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranose (2.0 g, 5.49 mmoL) in chloroform (40 mL), 3,4-dihydro-2H-pyran (1.5 mL, 16.5 mmoL) and p-toluenesulfonic acid monohydrate (104 mg, 0.549 mmoL) were added and stirred at room temperature for 1 hour. After addition of saturated aqueous sodium bicarbonate, the reaction mixture was extracted with chloroform, and the organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. After filtering off the desiccant, the solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the titled compound (2.56 g) as a light-yellow amorphous substance.

Workup

  1. extractionthe reaction mixture was extracted with chloroform
  2. washthe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtering off the desiccant
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-44f5338993ce48b49bfefea3ef09592d
Source dataset
uspto-grants-2012_02
Patent number
US08115017B2

Reaction notes

Loading…