Trichloroacetonitrile → HCID 10962910, compound

HRID 2086331Notes

Reaction equation

HRID 2086331 reaction equation
[C:1]([O:4][C@H:5]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:10]([CH2:16][O:17][C:18](=[O:20])[CH3:19])[O:9][CH:7]([OH:8])[C@@H:6]1[N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31])(=[O:3])[CH3:2].[Cl:32][C:33]([Cl:37])([Cl:36])[C:34]#[N:35].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Cl:32][C:33]([Cl:37])([Cl:36])[C:34](=[NH:35])[O:8][C@@H:7]1[O:9][C@H:10]([CH2:16][O:17][C:18](=[O:20])[CH3:19])[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:5]([O:4][C:1](=[O:3])[CH3:2])[C@H:6]1[N:21]1[C:22](=[O:31])[C:23]2=[CH:30][CH:29]=[CH:28][CH:27]=[C:24]2[C:25]1=[O:26]

Participants

5

Reactant 3

HCID 11011TrichloroacetonitrileHCID 11430Potassium CarbonateHCID 109282243,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

Product 1

HCID 10962910HCID 10962910, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 36 (4.0 g, 6.98 mmol) and trichloroacetonitril (4.2 ml, 14.88 mmol) in CH2Cl2 (25 ml) 18 g of finely powdered dry K2CO3 are added. After stirring for 60 min at RT the mixture is filtered through Celite®. Chromatography (silica gel, 500 g, hexane/ethyl acetate=2:1) gives 37 (β-anomer).

Workup

  1. additionare added
  2. filtrationis filtered through Celite®

Sources & evidence

ORD record
ord-589e4b30473b479ea8dc14c097a49d3e
Source dataset
uspto-grants-2004_04
Patent number
US06723831B2

Reaction notes

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