1-Phospha-sugars are analogs in which the anomeric carbon atom is replaced by a phosphorus atom. Cyclic phosphonate analogs also know as phostones have received continued attention in the literature mainly due to they are potential inhibitors of glycosidases. Phosphinosugars (phostines) are considered as mimes of glycosides and have shown anticancer activities. Of special interest are 2-deoxy-1-phospha-sugars that possess a certain structural relation with ß-KDO and the sialic acids in general. Herein we report on a new general methodology for the synthesis of phostones and phostines that has been developed in only four steps starting from glycals. The alkoxyl radical fragmentation (ARF) reaction of carbohydrate anomeric alcohols with hypervalent iodine reagents in the presence of iodine has been investigated by this laboratory and used as key step. Following the literature glycals can be converted to 2,3-dideoxy-hexopyranoses. The anomeric ARF of these compounds gave iodo compounds in high yields. Organophosphorus were obtained by Arbuzov reaction that followed by saponification of the formyl ester and subsequent cyclization produce 1-phospha-sugars in good yields.

Comunicación presentada en el XI Congreso de Estudiantes de la Facultad de Química celebrado en La Laguna (España) del 31 de marzo al 2 de abril de 2014.

Peer Reviewed