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

HRID 1711205Notes

Reaction equation

HRID 1711205 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. 1HNMR(DMSO-d6): 7.8 (d,2H,Ar—H,J=8.6 Hz), 7.5 (d,2H,Ar—H,J=8.6 Hz), 4.8-4.9 (m,2H,H-3, 6-OH), 4.4 (dd,1H,H-3a,J=4.7 and 5.0 Hz), 4.2 (dd,1H,H-6a,J=4.7 and 4.8 Hz), 3.9-4.0 (m,1H,H-6), 3.7-3.8 (m,2H,H-2 and H-5), 3.6 (d,1H,H-2,J=9.3 and 7.1 Hz),3.2-3.4(m,1H,H-5), 2.4 (s, 3H, Ar—CH3).

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-4c4164987b10420ab90268bae5ad2b96
Source dataset
uspto-grants-2010_09
Patent number
US07790749B2

Reaction notes

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