Trichloroacetonitrile → O-(2,3,4-tri-O-acetyl-beta-L-fucopyranosyl) trichloroacetimidate

HRID 1491954Notes

Reaction equation

HRID 1491954 reaction equation
[C:1]([O:4][C@H:5]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@H:9]([CH3:20])[O:8][CH:6]1[OH:7])(=[O:3])[CH3:2].[Cl-].[Li+].N12CCCN=C1CCCCC2.[Cl:34][C:35]([Cl:39])([Cl:38])[C:36]#[N:37]>C(#N)C>[Cl:34][C:35]([Cl:39])([Cl:38])[C:36](=[NH:37])[O:7][C@H:6]1[O:8][C@@H:9]([CH3:20])[C@@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:5]1[O:4][C:1](=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 11011TrichloroacetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 433294Lithium ChlorideHCID 10979132GlyTouCan:G58715BY

Product 1

HCID 14216865O-(2,3,4-tri-O-acetyl-beta-L-fucopyranosyl) trichloroacetimidateYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,3,4-tri-O-acetyl-L-fucopyranose (anomer mixture) (0.50 g, 1.72 mmol), lithium chloride (73 mg, 1.72 mmol), 1,8-diazabicyclo-[5.4.0]-undec-7-ene (0.20 ml, 1.34 mmol) and trichloroacetonitrile (2.0 ml, 20 mmol) in 20 ml of dry acetonitrile is stirred under nitrogen and at room temperature for about 12 h. After chromatographic purification (petroleum ether/diethyl ether 2:5), a mixture of O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl) trichloroacetimidate (3) and O-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl) trichloroacetimidate (2) is obtained in a yield of 92% (α:β=6.5:1).

Workup

  1. customAfter chromatographic purification (petroleum ether/diethyl ether 2:5)
  2. additiona mixture of O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl) trichloroacetimidate (3)

Sources & evidence

ORD record
ord-09ee4117809d465292bcc00bd44b18fc
Source dataset
uspto-grants-1994_12
Patent number
US05371203

Reaction notes

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