[4975-73-9] · C17H31N3O · N,N´-Dicyclohexyl-4-morpholinecarboximidamide · (MW 293.45)
(strong base; used as a catalyst for phosphorylation reactions in nucleoside chemistry)
Alternate Names: N,N´-dicyclohexyl-4-morpholineformamidine; DMC.
Physical Data: mp 105.5 °C.
Solubility: sol pyridine.
Form Supplied in: white powder.
Preparative Methods: easily prepared by refluxing morpholine and 1,3-Dicyclohexylcarbodiimide.1
DMC is a strong base that acts as a catalyst for phosphorylating reactions. It can be used to increase the solubility of salts of nucleoside 5´-phosphoromorpholidates, and to catalyze their cyclization to cyclic 3´,5´-nucleoside phosphates in the presence of DCC (eq 1).2
Reaction of DMC salts of nucleoside 5´-phosphoromorpholidates with phosphomonoesters gives nucleoside diphosphate derivatives.3 Similar reactions have been used for the synthesis of neosamine C-nucleoside diphosphates (eq 2).4
Preliminary formation of a morpholidate is not a necessary requirement and cyclization to 3´,5´-monophosphate derivatives is possible from DMC salts of the corresponding 5´-monophosphate. Ring closure is obtained by action of DCC in dry pyridine (eq 3).5
DMC catalyzes acylation of nucleosides by carboxylic anhydrides. As an example, reaction with succinic anhydride gives a mixture of isomers but refined conditions have been described to yield N6-succinyl adenosine (eq 4).6
DMC allows simultaneous 2-hydroxybenzylation and phosphorylation when used together with methylthio-4H-1,2,3-benzodioxaphosphorin 2-oxide (MTBO) (eq 5).7
Institut Pasteur, Lille, France.