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Synthesis 2024; 56(07): 1097-1138
DOI: 10.1055/s-0042-1751509
DOI: 10.1055/s-0042-1751509
short review
Emerging Trends in Glycoscience
Advances in the Synthesis of Spirocyclic Nucleosides
Sumit Kumar (SRF, File No.: 09/045(1798)/2020-EMR-I) and Aditi Arora (JRF, File No.: 09/0045(11270)/2021-EMR-I) have received awards from the Council of Scientific and Industrial Research (CSIR), New Delhi, India, and they are appreciative of the organization. We appreciate the Institute of Imminence at the University of Delhi for providing financial support to bolster research and development.
Dedicated to Late Professor Ashok K. Prasad, Department of Chemistry, University of Delhi, India.
Abstract
The nucleosides are the building blocks for nucleic acids and composed of a five-carbon sugar bearing either pyrimidine or purine nucleobase. The biological properties of nucleosides can be tailored by chemically modifying the five-carbon sugar to influence its sugar pucker. The spirocyclic scaffold is an indispensable scaffold in more than ten approved drugs, and its inherent three-dimensionality makes it an ideal modification to influence the sugar pucker and biological properties of nucleosides. However, the introduction of spirocyclic scaffold is often synthetically challenging due to increase in synthetic steps and stereocenters. The present review highlights the advances in synthetic methodologies developed during the past decades for accessing various members of the spiro-functionalized nucleoside family.
1 Introduction
2 C-1′-Spirocyclic Nucleosides
3 C-2′-Spirocyclic Nucleosides
4 C-3′-Spirocyclic Nucleosides
5 C-4′-Spirocyclic Nucleosides
6 Miscellaneous Spirocyclic Nucleosides
7 Conclusion and Future Perspectives
Key words
sugar-modified nucleoside - hydantocidin - spironucleoside - spirocyclic scaffold - Vorbrüggen glycosylation - chemoenzymatic synthesisPublication History
Received: 29 July 2023
Accepted after revision: 08 September 2023
Article published online:
16 November 2023
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