title: Synthesis of a pseudodisaccharide α-C-glycosidically linked to an 8-alkylated guanine.
abstract: The synthesis of stable guanofosfocin analogues has attracted considerable attention in the past 15 years. Several guanofosfocin analogues 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 analogue 6, an ether-linked pseudodisaccharide connected α-C-glycosidically to an 8-alkylated guanine, was synthesized in a 10-longest linear step sequence from known diol 13, resulting in an overall yield of 26%. The key steps involve the ring-opening of cyclic sulfate 8 by alkoxide generated from 7 and a reductive cyclization of 4-N-acyl-2,4-diamino-5-nitrosopyrimidine 19 to form compound 6.
authors.affiliation: School of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, China. mhhuang@bit.edu.cn
authors.forename: Mu-Hua
authors.initials: MH
authors.lastname: Huang
authors.forename: Jan
authors.initials: J
authors.lastname: Duchek
authors.forename: Andrea
authors.initials: A
authors.lastname: Vasella
mesh_terms: D000478:Alkylation; D003500:Cyclization; D004187:Disaccharides / Q000138:chemical synthesis*; D006147:Guanine / Q000737:chemistry; D008358:Mannose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D011743:Pyrimidines / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: C104367:2,4-diamino-6-benzyloxy-5-nitrosopyrimidine; D004187:Disaccharides; D011743:Pyrimidines; C479167:guanofosfocin; D006147:Guanine; D008358:Mannose
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