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    • (𝑆)-Garner aldehyde derived Baylis-Hillman adduct: A potential substrate for the synthesis of D-$lyxo$ phytosphinosine analogue

      Gulshan Kumar Amanpreet Kaur Vasundhara Singh

      Regular Articles Volume 126 Issue 6 November 2014 pp 1841-1847

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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/126/06/1841-1847

    • Keywords

       

      Baylis-Hillman acetates; decylmagnesium bromide; (S)-garner aldehyde; D-lyxophytosphingosine; OsO4/NMO dihydroxylation.

    • Abstract

       

      A short, facile and efficient synthesis of D-lyxo-phytosphingosine analogue has been achieved. The key steps involved are the Baylis-Hillman reaction of (S)-Garner aldehyde with methyl acrylate to obtain the corresponding adduct as the potential substrate, to which was added decylmagnesium bromide to obtain the E-trisubstituted alkene followed by OsO4/NMO mediated dihydroxylation gave the desired D-lyxophytosphingosine analogue intermediate diol which on acid hydrolysis resulted in the formation of the target molecule in good yield.

    • Author Affiliations

       

      Gulshan Kumar1 Amanpreet Kaur1 Vasundhara Singh1

      1. Department of Applied Sciences (Chemistry), PEC University of Technology, Chandigarh 160 012, India

    • Dates

       
      Published
      November 2014
      Manuscript received
      3 February 2014
      Manuscript revised
      19 April 2014
      Accepted
      25 April 2014

    • Supplementary Material

       

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