A Stereoselective Synthesis of α - and β-2′-Deoxy-2-thiouridine |
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| Authors: | Robert G Kuimelis Håkon Hope Krishnan P Nambiar |
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| Institution: | Department of Chemistry , University of California , Davis, 95616 |
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| Abstract: | Abstract A stereoselective glycosylation procedure is described for the synthesis of protected α- and β-2′-deoxy-2-thiouridine (dS2U) in 68% and 94% yield, respectively. Evidence is presented that suggests the reaction proceeds through a silylated thio-glycoside intermediate. This intermediate undergoes an efficient S2 → N1 rearrangement mediated by SnCl4. The phosphoramidite and phosphodiester synthons and a dS2U dinucleotide are also synthesized and the X-ray structure of β-dS2U is presented. |
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