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

HRID 416120ノート

反応式

HRID 416120 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a44d2e1e38004f2081f010fb22461f1e
出典データセット
uspto-grants-2012_01
特許番号
US08088823B2

反応ノート

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