Caecilie Benckendorff c.benckendorff@keele.ac.uk
Preparation of a 4′‐Thiouridine Building‐Block for Solid‐Phase Oligonucleotide Synthesis
Benckendorff, Caecilie M. M.; Sanghvi, Yogesh S.; Miller, Gavin J.
Authors
Yogesh S. Sanghvi
Gavin Miller g.j.miller@keele.ac.uk
Abstract
Starting from a commercially available thioether, we report a nine‐step synthesis of a 4′‐thiouridine phosphoramidite building‐block. We install the uracil nucleobase using Pummerer‐type glycosylation of a sulfoxide intermediate followed by a series of protecting group manipulations to deliver the desired phosphite. Notably, we introduce a 3′,5′‐O‐di‐tert‐butylsilylene protecting group within a 4′‐thiosugar framework, harnessing this to ensure regiospecific installation of the 2′‐O‐silyl protecting group. We envisage this methodology will be generally applicable to other 4′‐thionucleosides and duly support the exploration of their inclusion within related nucleic acid syntheses. © 2023 The Authors. Current Protocols published by Wiley Periodicals LLC. Basic Protocol 1: (2R,3S,4R)‐2,3‐O‐Isopopropylidene‐5‐O‐tert‐butyldiphenylsilyl‐1‐(4‐sulfinyl)cyclopentane: Sulfoxidation Basic Protocol 2: 2′,3′‐O‐Isopropylidene‐5′‐O‐tert‐butyldiphenylsilyl‐4′‐thiouridine: Pummerer glycosylation Basic Protocol 3: 4′‐Thiouridine: Deprotection Basic Protocol 4: 2′‐O‐tert‐Butyldimethylsilyl‐3′,5′‐di‐tert‐butylsiloxy‐4′‐thiouridine: 2′,3′,5′‐O‐silylation Basic Protocol 5: 2′‐O‐tert‐Butyldimethylsilyl‐4′‐thiouridine: Selective 3′‐5′‐desilylation Basic Protocol 6: 2′‐O‐tert‐Butyldimethylsilyl‐5′‐O‐dimethoxytrityl‐4′‐thiouridine: 5′‐O‐dimethoxytritylation Basic Protocol 7: 2′‐O‐tert‐butyldimethylsilyl‐3′‐O‐[(2‐cyanoethoxy)(N, N‐diisopropylamino)phosphino]‐5′‐O‐dimethoxytrityl‐4′‐thiouridine: 3′‐O‐phosphitylation
Citation
Benckendorff, C. M. M., Sanghvi, Y. S., & Miller, G. J. (2023). Preparation of a 4′‐Thiouridine Building‐Block for Solid‐Phase Oligonucleotide Synthesis. Current Protocols in Neuroscience, 3(9), Article e878. https://doi.org/10.1002/cpz1.878
Journal Article Type | Article |
---|---|
Acceptance Date | Sep 1, 2023 |
Online Publication Date | Sep 25, 2023 |
Publication Date | Sep 1, 2023 |
Deposit Date | Oct 9, 2023 |
Publicly Available Date | Oct 9, 2023 |
Journal | Current Protocols |
Print ISSN | 1934-8576 |
Publisher | Wiley |
Peer Reviewed | Peer Reviewed |
Volume | 3 |
Issue | 9 |
Article Number | e878 |
DOI | https://doi.org/10.1002/cpz1.878 |
Keywords | thiosugar, protecting group, phosphoramidite, 4′‐thionucleoside |
Public URL | https://keele-repository.worktribe.com/output/586883 |
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Preparation of a 4′‐Thiouridine Building‐Block for Solid‐Phase Oligonucleotide Synthesis
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This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
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