Synthesis 2017; 49(18): 4299-4302
DOI: 10.1055/s-0036-1588857
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of l-Ribose from d-Ribose by a Stereoconversion through Sequential Lactonization as the Key Transformation

Authors

  • Jaeyoung Ban

    a   Department of Bionanotechnology, Hanyang University, 55 Hanyangdaehak-ro, Sangnok-gu, Ansan, Gyeonggi-do 15588, South Korea
  • Saira Shabbir

    b   Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan
  • Minkyung Lim

    a   Department of Bionanotechnology, Hanyang University, 55 Hanyangdaehak-ro, Sangnok-gu, Ansan, Gyeonggi-do 15588, South Korea
  • Byunghoon Lee

    c   Department of Applied Chemistry, Hanyang University, 55 Hanyangdaehak-ro, Sangnok-gu, Ansan, Gyeonggi-do 15588, South Korea   Email: hrhee@hanyang.ac.kr
  • Hakjune Rhee*

    a   Department of Bionanotechnology, Hanyang University, 55 Hanyangdaehak-ro, Sangnok-gu, Ansan, Gyeonggi-do 15588, South Korea
    c   Department of Applied Chemistry, Hanyang University, 55 Hanyangdaehak-ro, Sangnok-gu, Ansan, Gyeonggi-do 15588, South Korea   Email: hrhee@hanyang.ac.kr
Further Information

Publication History

Received: 14 April 2017

Accepted after revision: 08 May 2017

Publication Date:
20 June 2017 (online)


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These authors contributed equally to this work.

Abstract

l-Ribose, a key precursor of various l-nucleosides can only be synthesized from other sugars or other non-sugar precursors. Herein, the study involves the synthesis of naturally rare l-ribose from readily available d-ribose. Though, many synthetic strategies are developed to meet the increasing demands of l-ribose, seeking innovation, a synthesis employing sequential lactonization as the key transformation was explored. This novel conversion involves protection, oxidation, sequential lactonization, reduction with DIBAL-H, and deprotection.

Supporting Information