Trichloroacetonitrile → 2,3,4-Tri-o-acetyl-alpha-l-fucopyranosyl trichloroacetimidate

HRID 1491953Notes

Reaction equation

HRID 1491953 reaction equation
[H-].[Na+].[C:3]([O:6][C@H:7]1[C@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:12]([O:18][C:19](=[O:21])[CH3:20])[C@H:11]([CH3:22])[O:10][CH:8]1[OH:9])(=[O:5])[CH3:4].[Cl:23][C:24]([Cl:28])([Cl:27])[C:25]#[N:26]>ClCCl>[Cl:23][C:24]([Cl:28])([Cl:27])[C:25](=[NH:26])[O:9][C@@H:8]1[O:10][C@@H:11]([CH3:22])[C@@H:12]([O:18][C:19](=[O:21])[CH3:20])[C@@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@@H:7]1[O:6][C:3](=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 11011TrichloroacetonitrileHCID 24758Sodium hydrideHCID 10979132GlyTouCan:G58715BY

Product 1

HCID 117297712,3,4-Tri-o-acetyl-alpha-l-fucopyranosyl trichloroacetimidateYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium hydride (0.25 g, 10.9 mmol) is added under nitrogen and at room temperature to a mixture of 2,3,4-tri-O-acetyl-L-fucopyranose (anomer mixture) (2.00 g, 6.89 mmol) and trichloroacetonitrile (7.0 ml, 70 mmol) in 20 ml of dry dichloromethane. The mixture is stirred for about 12 h and then filtered through kieselguhr and concentrated. After chromatographic purification (petroleum ether/ethyl acetate 3:1), O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl) trichloroacetimidate (3) is obtained in a yield of 71% (2.13 g).

Workup

  1. filtrationfiltered through kieselguhr
  2. concentrationconcentrated
  3. customAfter chromatographic purification (petroleum ether/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-72ed2f4f579943f1b70f80678550f0b4
Source dataset
uspto-grants-1994_12
Patent number
US05371203

Reaction notes

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