4.5 Article

Stereoselective Synthesis of 1-Thio-α-D-Ribofuranosides Using Ribofuranosyl Iodides as Glycosyl Donors

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 45, Pages 6355-6362

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201801201

Keywords

Diastereoselectivity; Ribofuranosides; Synthesis design; Thiols; Glycosylation

Funding

  1. Toyota Riken Scholar Program
  2. Koshiyama Research Grant

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A method for the 1,2-cis-selective synthesis of 1-thio-alpha-ribofuranosides has been developed. Ribofuranosyl iodides as glycosyl donors react effectively with thiols under mild basic conditions to afford various 1-thio-alpha-ribofuranosides, including some that are unstable under acidic conditions.

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