Water → HCID 53850275、化合物

HRID 54194ノート

反応式

HRID 54194 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][CH:21]=1)[CH2:11][O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C([O:25][C@@H:26]([C@@H:29]([C@@H:34]([C@H:39]([CH3:44])[O:40][C:41](=[O:43])[CH3:42])[O:35][C:36](=[O:38])[CH3:37])[O:30][C:31](=[O:33])[CH3:32])[CH:27]=O)(=O)C.B(F)(F)F.CCOCC.O>ClCCCl>[C:41]([O:40][C@H:39]1[C@H:34]([O:35][C:36](=[O:38])[CH3:37])[C@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@H:26]([CH3:27])[O:25][C@H:44]1[O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][CH:21]=1)[CH2:11][O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:43])[CH3:42]

参加物

6

反応物 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 14701098L-Galactose, 6-deoxy-, 2,3,4,5-tetraacetateHCID 19958321Ethyl 3-(2-hydroxyphenyl)benzyloxyacetate

生成物 1

HCID 53850275HCID 53850275、化合物収率 61%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

Part C: Ethyl 3-(2-hydroxyphenyl)benzyloxyacetate (0.85 g, 2.97 mmol) was dissolved in 1,2-dichloroethane (25 ml) in a dry 50 ml flask. L-Fucose tetraacetate (1.97 g, 5.94 mmol) was added in one portion, then boron trifluoride etherate (1.86 ml, 14.84 mmol) was added slowly. The mixture was stirred under nitrogen overnight at room temperature then mixed with water (50 ml). The organic material was separated and the aqueous portion was extracted with dichloromethane (3×5 ml). The extracts were combined with the original organic fraction, dried (MgSO4) then concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, gradient elution hexane to 3:1 hexane/ethyl acetate) which provided 1.0 g (61%) of ethyl 3-(2-(2,3,4-tri-O acetyl-α-L-fucopyranosyloxy)phenyl)benzyloxyacetate.

後処理

  1. customThe organic material was separated
  2. extractionthe aqueous portion was extracted with dichloromethane (3×5 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationthen concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (SiO2, gradient elution hexane to 3:1 hexane/ethyl acetate) which

出典と根拠

ORDレコード
ord-8b24044829134d7eb2fa964c882a9cff
出典データセット
uspto-grants-1997_04
特許番号
US05622937

反応ノート

読み込み中…