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Synthesis 2024; 56(06): 1035-1041
DOI: 10.1055/s-0041-1738440
paper
Emerging Trends in Glycoscience

Chemoenzymatic Synthesis of arabino-Configured Bicyclic Nucleosides

Harbansh Singla
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
,
Jyotirmoy Maity
b   Department of Chemistry, St. Stephen’s College, University of Delhi, Delhi 110 007, India
,
Sandeep Kumar
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
,
Kavita Kavita
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
,
Riya Chaudhary
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
,
Ashok K. Prasad  ∗
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
› Author AffiliationsHarbansh Singla and Kavita thank CSIR, New Delhi for the award of a Senior research fellowship. We are grateful to Institute of Eminence, University of Delhi for providing financial support to strengthen research and development.
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Abstract

A convergent route for the synthesis of a new class of bicyclic nucleosides has been developed. The synthetic route to the corresponding arabino-configured uracil and thymine bicyclic nucleosides proceeds in 24 and 27% overall yields, respectively, starting from 1,2,5,6-di-O-isopropylidene-α-d-glucofuranose. This synthetic protocol includes some crucial steps such as Vorbrüggen base coupling and chemo-enzymatic regioselective acetylation of the primary hydroxyl group by using Lipozyme® TL IM where it was found that Lipozyme® TL IM could be recovered and reused for selective acetylation without losing its selectivity.

Key words

chemo-enzymatic pathway - regioselective monoacetylation - Lipozyme® TL IM - bicyclic nucleosides

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1738440.
  • Supporting Information


Publication History

Received: 07 February 2023

Accepted after revision: 20 April 2023

Article published online:
22 May 2023

© 2023. Thieme. All rights reserved

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