3,4-dihydro-2H-pyran → (3S,3aR,6S,6aR)-6-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol

HRID 1676008Notes

Reaction equation

HRID 1676008 reaction equation
[O:1]1[CH2:5][C@H:4]([OH:6])[C@H:3]2[O:7][CH2:8][C@H:9]([OH:10])[C@@H:2]12.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1>C(Cl)Cl>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:6][C@@H:4]1[C@H:3]2[O:7][CH2:8][C@H:9]([OH:10])[C@H:2]2[O:1][CH2:5]1

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 12304539(3S,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol

Product 1

HCID 58209398(3S,3aR,6S,6aR)-6-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol (0.57 g, 3.90 mmol) and 3,4-dihydro-2H-pyran (0.41 g, 4.88 mmol) in DCM (15 ml), toluene-4-solfonic acid monohydrate (0.0074 g, 0.039 mmol) was added and the mixture was stirred at room temperature for 3 hrs. Then the reaction mixture was washed with a saturated solution of NaHCO3 and brine. The organic extract was dried over sodium sulfate and the solvent, was evaporated under reduced pressure. The residue was purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 30 to 100%), affording the title product as a white solid.

Workup

  1. washThen the reaction mixture was washed with a saturated solution of NaHCO3 and brine
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulfate
  4. customthe solvent, was evaporated under reduced pressure
  5. customThe residue was purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 30 to 100%)

Sources & evidence

ORD record
ord-03a7126579e740bd9e6d3ddd90894b37
Source dataset
uspto-grants-2011_08
Patent number
US08003811B2

Reaction notes

Loading…