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

HRID 909767Notes

Reaction equation

HRID 909767 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[C:7]([O:10][C@@H:11]1[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:16]([O:22][C:23](=[O:25])[CH3:24])[C@@H:15]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[S:14][CH:12]1[OH:13])(=[O:9])[CH3:8].C(=O)(O)[O-].[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(Cl)(Cl)Cl>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[C:12]1([S:14][C@H:15]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[C@@H:16]([O:22][C:23](=[O:25])[CH3:24])[C@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:11]1[O:10][C:7](=[O:9])[CH3:8])[OH:13]

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 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-glucopyranoseYield 104%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6212ChloroformSolvent

Procedure

3,4-Dihydro-2H-pyran (1.5 mL, 16.5 mmol) and p-toluenesulfonic acid monohydrate (104 mg, 0.549 mmol) were added to a chloroform (40 mL) solution of 2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranose (2.0 g, 5.49 mmol) and stirred at room temperature for one hour. The reaction mixture was added with a saturated sodium bicarbonate aqueous solution and extracted with chloroform, and after the organic layer was washed with brine, it was dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain pale yellow amorphous tetrahydro-2H-pyran-2-yl 2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranose (2.56 g).

Workup

  1. extractionextracted with chloroform
  2. washafter the organic layer was washed with brine, it
  3. dry with materialwas dried with anhydrous magnesium sulfate
  4. filtrationAfter the desiccant was filtered off
  5. customthe residue obtained
  6. customby evaporating the solvent under reduced pressure
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-6fdfd720972b4a52b55b00f3292bf75f
Source dataset
uspto-grants-2011_09
Patent number
US08017792B2

Reaction notes

Loading…