p-Toluenesulfonic acid → (1S,5R,6R,7R)-6-(3,3-ethylenedioxyoctyl)-7-tetrahydropyranyloxy-2-oxabicyclo[3.3.0]octan-3-one

HRID 21920ノート

反応式

HRID 21920 の反応式
[CH2:1]1[CH2:22][O:21][C:3]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])([CH2:4][CH2:5][C@H:6]2[C@H:13]([OH:14])[CH2:12][C@H:11]3[C@@H:7]2[CH2:8][C:9](=[O:15])[O:10]3)[O:2]1.[O:23]1[CH:28]=[CH:27][CH2:26][CH2:25][CH2:24]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[CH2:1]1[CH2:22][O:21][C:3]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])([CH2:4][CH2:5][C@H:6]2[C@H:13]([O:14][CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28][O:23]3)[CH2:12][C@H:11]3[C@@H:7]2[CH2:8][C:9](=[O:15])[O:10]3)[O:2]1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 14674517HCID 14674517、化合物

生成物 1

HCID 14674520(1S,5R,6R,7R)-6-(3,3-ethylenedioxyoctyl)-7-tetrahydropyranyloxy-2-oxabicyclo[3.3.0]octan-3-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (1S,5R,6R,7R)-6-(3,3-ethylenedioxyoctyl)-7-hydroxy-2-oxabicyclo[3.3.0]octan-3-one (6a) (4.70 g) in dichloromethane (200 ml) was cooled on ice and dihydropyran (2.41 g) and p-toluenesulfonic acid (0.23 g) were added thereto and the resultant mixture was stirred for 1,5 hours. The crude product obtained by treating in the conventional manner was subjected to silica gel column chromatography to give the title compound (59).

後処理

  1. additionwere added
  2. customThe crude product obtained
  3. additionby treating in the conventional manner

出典と根拠

ORDレコード
ord-6d47b3eb15aa48628a928ca6cb40ca21
出典データセット
uspto-grants-1995_06
特許番号
US05426115

反応ノート

読み込み中…