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Stereoselective Syntheses of 3’-Hydroxyamino- and 3’-Methoxyamino-2’,3’-Dideoxynucleosides

Bose, Sritama; Hodgson, David R.W.

Stereoselective Syntheses of 3’-Hydroxyamino- and 3’-Methoxyamino-2’,3’-Dideoxynucleosides Thumbnail


Sritama Bose


Aminonucleosides are used as key motifs in medicinal and bioconjugate chemistry; however, existing strategies toward 3′-hypernucleophilic amine systems do not readily deliver deoxyribo-configured products. We report diastereoselective syntheses of deoxyribo- and deoxyxylo-configured 3′-hydroxyamino- and 3′-methoxyamino-nucelosides from 3′-imine intermediates. The presence or absence of the 5′-hydroxyl-group protection dictates facial selectivity via inter- or intramolecular delivery of hydride from BH3 (borane). Protecting group screening gave one access to previously unknown 3′-methoxyamino-deoxyguanosine derivatives.


Bose, S., & Hodgson, D. R. (2019). Stereoselective Syntheses of 3’-Hydroxyamino- and 3’-Methoxyamino-2’,3’-Dideoxynucleosides. Organic Letters, 21(22), 9084-9088.

Journal Article Type Article
Acceptance Date Oct 29, 2019
Online Publication Date Oct 31, 2019
Publication Date Nov 15, 2019
Deposit Date Oct 29, 2019
Publicly Available Date Nov 1, 2019
Journal Organic Letters
Print ISSN 1523-7060
Electronic ISSN 1523-7052
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 21
Issue 22
Pages 9084-9088


Published Journal Article (Advance online version) (876 Kb)

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Copyright Statement
Advance online version This is an open access article published under a Creative Commons Attribution (CC-BY)<br /> License, which permits unrestricted use, distribution and reproduction in any medium,<br /> provided the author and source are cited.

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