Water → HCID 53850275, compound

HRID 54194Notes

Reaction equation

HRID 54194 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 53850275HCID 53850275, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8b24044829134d7eb2fa964c882a9cff
Source dataset
uspto-grants-1997_04
Patent number
US05622937

Reaction notes

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