Glyoxal → delta-Gluconolactone

HRID 46212

反応式

HRID 46212 の反応式
ClC1C=CC([C@H:8]2[C@H:13]([O:14]CC3C=CC=CC=3)[C@@H:12]([O:22]CC3C=CC=CC=3)[C@H:11]([O:30]CC3C=CC=CC=3)[C@@H:10]([CH2:38][O:39]CC3C=CC=CC=3)[O:9]2)=CC=1CC(=N)NN.C(C=O)=[O:53]>CCO>[CH2:38]([OH:39])[C@H:10]1[O:9][C:8](=[O:53])[C@H:13]([OH:14])[C@@H:12]([OH:22])[C@@H:11]1[OH:30]

参加物

4

反応物 2

HCID 7860GlyoxalHCID 178510822HCID 178510822、化合物2 回

生成物 1

HCID 7027delta-Gluconolactone収率 60%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)acetimidohydrazide (compound 45, crude 1 g from step 1) in EtOH (30 ml) reacted with glyoxal (5 ml, 30% in water) at 0° C., and allowed to warm up at room temperature. After the reaction mixture was stirred for 3 hours, it was evaporated under reduced pressure to remove volatile compounds. The residue was purified with silica gel (Hx/EtOAc=⅓) to provided title compound (324 mg, 60% overall yield form intermediate 2).

後処理

  1. customit was evaporated under reduced pressure
  2. customto remove volatile compounds
  3. customThe residue was purified with silica gel (Hx/EtOAc=⅓)

出典と根拠

ORDレコード
ord-dccbd57b1b6343c194f85b8bf62d9678
出典データセット
uspto-grants-2013_09
特許番号
US08541380B2

関連ノート

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