Synthesis of a pseudodisaccharide α-C-glycosidically linked to an 8-alkylated guanine.
writer：Huang, Mu-Hua Duchek, Jan Vasella, Andrea.
keywords：alkylated guanine C glycoside pseudodisaccharide prepn
source：期刊
specific source：Molecules
Issue time：2013年
The synthesis of stable guanofosfocin analogs has attracted considerable attention in the past 15 years. Several guanofosfocin analogs mimicking the three constitutional elements of mannose, ribose and guanine were designed and synthesized. Interest in ether-linked pseudodisaccharides and 8-alkylated guanines is increasing, due to their potential applications in life science. In this article, a novel guanofosfocin analog, an ether-linked pseudodisaccharide connected α-C-glycosidically to an 8-alkylated guanine, was synthesized in a 10-longest linear step sequence from a known diol, resulting in an overall yield of 26%. The key steps involve the ring-opening of cyclic sulfate by alkoxide generated from a C-allyl glycoside and a reductive cyclization of 4-N-acyl-2,4-diamino-5-nitrosopyrimidine to form the target compd. [on SciFinder(R)]