Water → HCID 53850275, 화합물

HRID 54194노트

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HRID 54194 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 53850275HCID 53850275, 화합물수율 61%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8b24044829134d7eb2fa964c882a9cff
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622937

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