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

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.