4.7 Article

Unified Strategy toward Stereocontrolled Assembly of Various Glucans Based on Bimodal Glycosyl Donors

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 8, Pages 5536-5558

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00292

Keywords

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Funding

  1. Ministry of Education, Culture, Sports, Science, and Technology [16H06290]
  2. Japan Society for the Promotion of Science [26350966, 15H02443]
  3. RIKEN
  4. Fundamental Research Funds for the Central Universities from China [75110-31610011]
  5. Sun Yatsen University Startup fund [75110-18841224]
  6. Grants-in-Aid for Scientific Research [16H06290, 26350966] Funding Source: KAKEN

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Polymers of glucose, the most abundant and one of the biologically important natural products, named glucans are widely present in fungi, bacteria, mammals, and plants with various anomeric configurations and glycosidic linkages. Because of their structural diversity, the unified strategy for the assembly of pure glucans is yet to be developed. Herein, we describe a general strategy that is applicable to construction of all types of glucans by exploiting a bimodal glycosyl donor equipped with C2-o-TsNHbenzyl ether (TAB), which enables stereocontrolled synthesis of both alpha- and beta-glycosides by switching reaction conditions.

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