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Synlett 1995; 1995(10): 1053-1054
DOI: 10.1055/s-1995-5165
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A New Approach to the Synthesis of 4-Thio-1,2-Dideoxyribose

Ian A. O’Neil* , Kathryn M. Hamilton, J. Allen Miller
  • *Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, P.O. Box 147, Liverpool L69 3BX, U.K.
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Publication Date:
31 December 2000 (online)

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A novel approach to the synthesis of racemic 4-thio-1,2-deoxyribose (1) is described. Thus, commercially available γ-thiobutyrolactone is converted to the thiolenol triflate (3) and then to the key 5-(hydroxymethyl)-2,3-dihydrothiophene (2). Hydroboration followed by oxidative work up gives the desired product (1) in four steps.

Thiosugar - vinyl stannane - vinyl triflate