title: Transformation of the (2-nitrophenyl)acetyl protecting group in the presence of trichloroacetonitrile and 1,8-diazabicyclo[5,4,0]-undec-7-ene.
abstract: When treated with trichloroacetonitrile in the presence of 1,8-diazabicyclo[5,4,0]-undec-7-ene, the (2-nitrophenyl)acetyl protecting group (NPAc) was partially transformed into mono-(NPClAc) and dichlorinated (NPCl₂Ac) species, but no chlorination occurred in the presence of solid potassium carbonate. The monochlorinated NPClAc group, which is suitable for use in glycosylation reaction, can be selectively removed by treatment with thiourea.
authors.affiliation: Institut de Chimie Organique et Analytique, UMR 7311 CNRS et Université d'Orléans, LabEx «SynOrg», Pôle de Chimie, Université d'Orléans, BP 6759, 45067 Orléans Cedex 2, France. Jean-Claude.Jacquinet@univ-orleans.fr
authors.forename: Jean-Claude
authors.initials: JC
authors.lastname: Jacquinet
mesh_terms: D000097:Acetonitriles / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000097:Acetonitriles; D019086:Bridged Bicyclo Compounds, Heterocyclic; C029549:trichloroacetonitrile; C031033:1,8-diazabicyclo(5.4.0)undec-7-ene