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Synthesis 2024; 56(06): 1035-1041
DOI: 10.1055/s-0041-1738440
DOI: 10.1055/s-0041-1738440
paper
Emerging Trends in Glycoscience
Chemoenzymatic Synthesis of arabino-Configured Bicyclic Nucleosides
Harbansh 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.
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 nucleosidesSupporting 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
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