Ethanol → 4,6-dichloro-1-(beta-D-glucopyranosyl)indoline

HRID 544889ノート

反応式

HRID 544889 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][NH:6]2.[O:12]=[CH:13][C@@H:14]([C@H:16]([C@@H:18]([C@@H:20]([CH2:22][OH:23])[OH:21])[OH:19])[OH:17])O.C(O)C>O>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[C@@H:22]1[O:23][C@H:14]([CH2:13][OH:12])[C@@H:16]([OH:17])[C@H:18]([OH:19])[C@H:20]1[OH:21]

参加物

5

反応物 3

HCID 702EthanolHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 162444484,6-Dichloroindoline

生成物 1

HCID 671990964,6-dichloro-1-(beta-D-glucopyranosyl)indoline

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 4,6-dichloroindoline (6.57 g) and D-glucose (10.70 g) in H2O (25 ml)-ethyl alcohol (160 ml) was refluxed for 3 days. The organic solvent was evaporated under reduced pressure, and thereto were added brine and ammonium sulfate. The mixture was extracted with ethyl acetate 5 times, and the combined organic layer was dried over sodium sulfate. The insoluble materials were filtered off, and the filtrate was evaporated under reduced pressure to give crude 4,6-dichloro-1-(β-D-gluco-pyranosyl)indoline, which was used in the subsequent step without further purification.

後処理

  1. temperaturewas refluxed for 3 days
  2. customThe organic solvent was evaporated under reduced pressure
  3. additionwere added brine and ammonium sulfate
  4. extractionThe mixture was extracted with ethyl acetate 5 times
  5. dry with materialthe combined organic layer was dried over sodium sulfate
  6. filtrationThe insoluble materials were filtered off
  7. customthe filtrate was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-0a36bfbe0868476f83a030ff3e05d35d
出典データセット
uspto-grants-2011_05
特許番号
US07935674B2

反応ノート

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