Pyridine → (3R,3aS,6R,6aR)-6-Hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate

HRID 416120Notes

Reaction equation

HRID 416120 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.[C:11]1(C)[C:12]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=1.N1C=CC=C[CH:23]=1>>[OH:6][C@H:4]1[C@H:3]2[O:7][CH2:8][C@@H:9]([O:10][S:17]([C:12]3[CH:11]=[CH:16][C:15]([CH3:23])=[CH:14][CH:13]=3)(=[O:18])=[O:19])[C@H:2]2[O:1][CH2:5]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 7269354(3R,3aS,6R,6aR)-hexahydro-furo[3,2-b]furan-3,6-diol

Product 1

HCID 13014014(3R,3aS,6R,6aR)-6-Hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate

Procedure

A solution of 5 g of (3R,3aS,6R,6aR)-hexahydro-furo[3,2-b]furan-3,6-diol in 50 ml of pyridine is stirred for 16 h with 7.8 g of toluenesulfonylchloride. From the mixture obtained solvent is distilled off and the distillation residue obtained is dissolved in EtAc and extracted with 1N HCl, saturated aqueous NaHCO3-solution and H2O. The organic layer obtained is dried, solvent is evaporated and the evaporation residue is subjected to chromatography. Toluene-4-sulfonic acid (3R, 3aS,6R,6aR)-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester is obtained.

Workup

  1. customFrom the mixture obtained solvent
  2. distillationis distilled off
  3. customthe distillation residue obtained
  4. dissolutionis dissolved in EtAc
  5. extractionextracted with 1N HCl, saturated aqueous NaHCO3-solution and H2O
  6. customThe organic layer obtained
  7. customis dried
  8. customsolvent is evaporated

Sources & evidence

ORD record
ord-a44d2e1e38004f2081f010fb22461f1e
Source dataset
uspto-grants-2012_01
Patent number
US08088823B2

Reaction notes

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