title: Synthesis of di-branched heptasaccharide by one-pot glycosylation using seven independent building blocks.
abstract: [reaction: see text] We describe an efficient synthesis of di-branched heptasaccharide 1 having phytoalexin elicitor activity in soybeans by one-pot glycosylation. The synthesis involves chemo- and regioselective sequential six-step glycosylations using seven independent building blocks and sequential removal of acyl- and benzyl ether-type protecting groups. The coupling of seven building blocks requires only four chemoselective activitable leaving groups of glycosyl donors. Both the glycosylation and deprotection reactions can be achieved utilizing a parallel manual synthesizer.
authors.affiliation: Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Tanaka
authors.forename: Masaatsu
authors.initials: M
authors.lastname: Adachi
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Tsukamoto
authors.forename: Takeji
authors.initials: T
authors.lastname: Ikeda
authors.forename: Haruo
authors.initials: H
authors.lastname: Yamada
authors.forename: Takashi
authors.initials: T
authors.lastname: Takahashi
mesh_terms: D002240:Carbohydrate Sequence; D006031:Glycosylation; D008969:Molecular Sequence Data; D025942:Oligosaccharides, Branched-Chain / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D010936:Plant Extracts / Q000378:metabolism; D012717:Sesquiterpenes; D013025:Glycine max / Q000187:drug effects / Q000378:metabolism; D013729:Terpenes; D000094162:Phytoalexins
chemical_list: D025942:Oligosaccharides, Branched-Chain; D010936:Plant Extracts; D012717:Sesquiterpenes; D013729:Terpenes; D000094162:Phytoalexins