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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.[1]

References

  1. Synthesis of di-branched heptasaccharide by one-pot glycosylation using seven independent building blocks. Tanaka, H., Adachi, M., Tsukamoto, H., Ikeda, T., Yamada, H., Takahashi, T. Org. Lett. (2002) [Pubmed]
 
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