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Synthesis 1989; 1989(7): 564-565
DOI: 10.1055/s-1989-27322
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A Facile Synthesis of (S)-3-Tosyloxy-1,2-propanediol from (S)-2,2-Dimethyl-1,3-dioxolane-4-methanol

Katerina Leftheris* , Murray Goodman
  • *Department of Chemistry B-043, University of California San Diego, La Jolla, CA 92093, USA
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Publication Date:
12 January 2006 (online)

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(S)-3-Tosyloxy-1,2-propanediol[(S)-2] has been synthesized from (S)-2,2-dimethyl-1,3-dioxolane-4-methanol [(S)-1] in four steps with an overall yield of 87%. This coupled with the existing method in the literature for the conversion of (S)-1 to (R)-2 allows both (R)- and (S)-2 to be readily available from either (S)- or (R)-1. The use of the tert-butyldiphenylsilyl protecting group permits two acid labile protecting groups to be incorporated simultaneously. Selective reactions and deprotections lead to the desired configuration.

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