Synthesis of di-branched heptasaccharide by one-pot glycosylation using seven independent building blocks.
[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.
Tanaka
Hiroshi
H
Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan.
Adachi
Masaatsu
M
Tsukamoto
Hirokazu
H
Ikeda
Takeji
T
Yamada
Haruo
H
Takahashi
Takashi
T
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
D025942:Oligosaccharides, Branched-Chain; D010936:Plant Extracts; D012717:Sesquiterpenes; D013729:Terpenes; D000094162:Phytoalexins