4.5 Article

C-Glycosylation of Substituted β-Naphthols with Trichloroacetimidate Glycosyl Donors

Journal

SYNTHESIS-STUTTGART
Volume 50, Issue 7, Pages 1560-1568

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1591746

Keywords

C-glycosylation; 2-naphthols; Lewis acids; trichloroacetimidate; glycosyl donors; substituent effects

Funding

  1. CSIR
  2. Council of Scientific and Industrial Research (CSIR) [02(0183)/14/EMRII]
  3. IIT Kharagpur

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Several glycosyl donors have been systematically investigated for C-glycosylation of substituted -naphthols to delineate the effect of the substituents. Whereas glycosylations of the parent 2-naphthol are smoothly achievable, those of differently substituted 2-naphthols are cumbersome. Efficiency of the glycosylation depends on the nature of both the glycosyl donors and the substituents of the arene ring. Among various glycosyl donors, trichloroacetimidate glycosyl donors are found to be superior for glycosylation with substituted 2-naphthols.

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