4.8 Article

ZnI2-Directed Stereocontrolled α-Glucosylation

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ORGANIC LETTERS
卷 23, 期 17, 页码 6841-6845

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02405

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资金

  1. Fundamental Research Funds for the Central Universities from China [75110-31610011]
  2. Sun Yat-sen University Startup fund [75110-18841224]
  3. Natural Science Foundation of Guangdong Province [75110-42030015]
  4. Japan Society for the Promotion of Science [16H06290, 18K05345, 19H00929]
  5. Grants-in-Aid for Scientific Research [18K05345, 19H00929] Funding Source: KAKEN

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This study presents a glucosylation strategy using ZnI2 for stereoselective construction of 1,2-cis-O-glycosidic linkages. The versatility of this approach was demonstrated with various acceptors, including complex alcohols, indicating the potential for modular synthesis of various alpha-glucans.
Here we report a glucosylation strategy mediated by ZnI2, a cheap and mild Lewis acid, for the highly stereoselective construction of 1,2-cis-O-glycosidic linkages using easily accessible and common 4,6-O-tethered glucosyl donors. The versatility and effectiveness of the alpha-glucosylation strategy were demonstrated successfully with various acceptors, including complex alcohols. This approach demonstrates the feasibility of the modular synthesis of various alpha-glucans with both linear and branched backbone structures.

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