Journal
TETRAHEDRON
Volume 75, Issue 37, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2019.130497
Keywords
L-Nucleosides; Nucleoside osphonates; Glycosylation
Categories
Funding
- China Scholarship Council (CSC) [201506890014]
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Structurally modified nucleoside analogues are a major source of therapeutic agents and building blocks for incorporation into synthetic oligonucleotides able to interfere with information transfer or other biological functions. This work describes the synthesis of non-natural L-nucleoside phosphonate mimics containing two anomeric centers. Such compounds feature either a di- or monohydroxy tetradialdose sugar as the glycone unit, while adenine is present as nucleobase. By judicious use of protecting groups at the 2- and 3-position of commercial 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose, both the phosphonate and nucleobase moieties were stereoselectively introduced to provide a dihydroxylated compound with cis-configured substituents as the sole reaction product. Subsequent selective deprotection and deoxygenation at the 3'-position occurred smoothly to afford the corresponding 4'-monohydroxy tetradialdose containing analogue. (C) 2019 Elsevier Ltd. All rights reserved.
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