trichloroacetimidate
Trichloroacetimidate refers to a class of organic imidates in which an alkoxy substituent is bound to a carbon that also bears a trichloroacetyl imidate moiety. In practice, the most important members are glycosyl trichloroacetimidates, formed from protected sugars and trichloroacetimidoyl chloride. These donors feature a leaving group on the anomeric position that can be activated under mild conditions to generate an oxocarbenium ion, enabling glycosylation with a wide range of alcohol acceptors.
Preparation of trichloroacetimidates typically involves condensation of an alcohol with trichloroacetimidoyl chloride in the presence of
Activation and use in glycosylation are the primary applications. Under catalytic amounts of Lewis or Brønsted
In summary, trichloroacetimidates, especially glycosyl donors, are key reagents in carbohydrate synthesis, offering a versatile, relatively
See also: acetimidate donors, Schmidt glycosylation, glycosylation.