Sodium Azide → (3R,3aR,6S,6aR)-6-azido-hexahydro-furo[3,2-b]furan-3-ol

HRID 416121ノート

反応式

HRID 416121 の反応式
[OH:1][C@H:2]1[C@H:6]2[O:7][CH2:8][C@@H:9](OS(C3C=CC(C)=CC=3)(=O)=O)[C@H:5]2[O:4][CH2:3]1.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C>[N:21]([C@@H:9]1[C@H:5]2[O:4][CH2:3][C@@H:2]([OH:1])[C@H:6]2[O:7][CH2:8]1)=[N+:22]=[N-:23]

参加物

4

反応物 2

HCID 33557Sodium AzideHCID 13014014(3R,3aS,6R,6aR)-6-Hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate

生成物 1

HCID 51345858(3R,3aR,6S,6aR)-6-azido-hexahydro-furo[3,2-b]furan-3-ol

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2.5 g of toluene-4-sulfonic acid (3R,3aS,6R,6aR)-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester in 30 ml of DMF is heated with 0.8 g of sodium azide under reflux for 2 hours, solvent is distilled off and the distillation residue obtained is dissolved in EtAc and extracted with H2O. The organic phase obtained is dried and solvent is evaporated. (3R,3aR,6S,6aR)-6-azido-hexahydro-furo[3,2-b]furan-3-ol is obtained.

後処理

  1. temperatureunder reflux for 2 hours
  2. distillationsolvent is distilled off
  3. customthe distillation residue obtained
  4. dissolutionis dissolved in EtAc
  5. extractionextracted with H2O
  6. customThe organic phase obtained
  7. customis dried
  8. customsolvent is evaporated

出典と根拠

ORDレコード
ord-0d499233193a460f93492120885ad6d3
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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