Cesium carbonate → (2S,3R,4R,5S,6R)-2-(3-(4-(2-(2-bromoethoxy)ethoxy)benzyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

HRID 425079ノート

反応式

HRID 425079 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38]Br>CN(C)C=O.O>[Br:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C:3]2[CH:4]=[C:5]([C@H:8]3[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]3)[CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:25][CH:24]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 21521Bis(2-bromoethyl) etherHCID 44580555Bms-5119262 回

生成物 1

HCID 59557753(2S,3R,4R,5S,6R)-2-(3-(4-(2-(2-bromoethoxy)ethoxy)benzyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol収率 21.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred suspension of (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (intermediate D1) (100 mg, 0.26 mmol) in N,N-dimethylformamide (3 mL) and cesium carbonate (162 mg, 0.52 mmol) was added 1-bromo-2-(2-bromoethoxy)ethane (182 mg, 0.79 mmol). The mixture was stirred overnight at room temperature. The solution was diluted with water and the aqueous layer was extracted with ethyl acetate. The combined organic layers were concentrated under reduced pressure. The residue was purified by preparative TLC to give 30 mg of yellow oil (21% yield), which was used in the next step without purification.

後処理

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. concentrationThe combined organic layers were concentrated under reduced pressure
  3. customThe residue was purified by preparative TLC

出典と根拠

ORDレコード
ord-be4e15b5e31c427bad6da1711471ccd0
出典データセット
uspto-grants-2012_01
特許番号
US08106021B2

反応ノート

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