Synthesis of di-branched heptasaccharide by one-pot glycosylation using seven independent building blocks |
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Authors: | Tanaka Hiroshi Adachi Masaatsu Tsukamoto Hirokazu Ikeda Takeji Yamada Haruo Takahashi Takashi |
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Institution: | Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan. |
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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. |
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