Convenient syntheses of symmetrical and unsymmetrical glycosyl carbodiimides and N,N-bis(glycosyl)cyanamides.
Reaction of glycosyl trimethylphosphinimides with carbon disulfide under mild conditions (room temperature, short reaction time) leads to symmetrical glycosyl carbodiimides. Addition of bis(trimethylsilyl)carbodiimide to peracetylated aldoses under the influence of SnCl(4) afforded N,N-bis(glycosyl)cyanamides for the first time. Readily accessible unsymmetrical N,N'-bis(glycosyl)thioureas can be desulfurated and transformed into the corresponding carbodiimides using HgO in CHCl(3)/water at room temperature.
Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, PO Box 20, Hungary.
László
L
Kovács
Erzsébet
E
Osz
Zoltán
Z
Györgydeák
D002234:Carbodiimides / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D003484:Cyanamide / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D002234:Carbodiimides; D006027:Glycosides; D003484:Cyanamide