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β-Stereoselective Mannosylation Using 2,6-Lactones.

Yusuke Hashimoto1, Saki Tanikawa1, Ryota Saito1

  • 1Department of Chemistry, Toho University , 2-2-1 Miyama, Funabashi 274-8510 Japan.

Journal of the American Chemical Society
|October 27, 2016
PubMed
Summary
This summary is machine-generated.

A novel 2,6-lactone strategy enables stereoselective β-mannosylation, overcoming the typical α-glycoside formation. This method utilizes glycosyl trichloroacetimidates and a unique catalyst system for efficient β-mannoside synthesis.

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Stereoselective Reactions

Background:

  • Glycosylation reactions typically favor α-glycoside formation due to stereoelectronic effects favoring SN1 mechanisms.
  • Achieving β-stereoselectivity in mannosylation is challenging but crucial for synthesizing biologically relevant glycoconjugates.

Purpose of the Study:

  • To develop a novel strategy for stereoselective β-mannosylation.
  • To investigate the utility of 2,6-lactone moieties in controlling glycosylation stereochemistry.

Main Methods:

  • Utilized glycosyl trichloroacetimidates as donors bearing a 2,6-lactone moiety.
  • Employed a combined catalyst system of AuCl3 and 3,5-bis(trifluoromethyl)phenyl thiourea.
  • Investigated the effect of reaction concentration on product stereoselectivity.

Main Results:

  • The 2,6-lactone moiety effectively suppressed the competing SN1 pathway, promoting β-glycoside formation via SN2(-like) mechanisms.
  • High β-stereoselectivity was achieved, with stereochemical outcome influenced by reaction concentration.
  • Even under SN1 conditions, the glycosyl cation exhibited a β-directing steric influence.

Conclusions:

  • The 2,6-lactone strategy is highly effective for achieving β-stereoselective mannosylation.
  • This approach offers a valuable tool for the synthesis of complex β-mannosides.
  • The findings provide insights into controlling stereochemistry in glycosylation reactions.