Synthesis of morpholino nucleosides starting from enantiopure glycidol

The synthesis of modified morpholino monomers was performed in a few steps through the condensation between 6-hydroxymethyl-morpholine acetal and nucleobases under Lewis acid conditions. The key common precursor of the targets – 6-hydroxymethyl-morpholine acetal – is easily synthesised via oxirane r...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2022-05, Vol.9 (11), p.2949-2954
Main Authors: Papis, Marta, Loro, Camilla, Penso, Michele, Broggini, Gianluigi, Foschi, Francesca
Format: Article
Language:English
Subjects:
Bases (nucleic acids)
Benzoylation
Cascade chemical reactions
Ethylene oxide
Lewis acid
Monomers
Morpholine
Nucleophiles
Nucleotide sequence
Organic chemistry
Ring opening
Synthesis
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Summary:The synthesis of modified morpholino monomers was performed in a few steps through the condensation between 6-hydroxymethyl-morpholine acetal and nucleobases under Lewis acid conditions. The key common precursor of the targets – 6-hydroxymethyl-morpholine acetal – is easily synthesised via oxirane ring opening of optically pure glycidol using N-nosyl aminoacetaldehyde as a nucleophile, followed by an O-benzoylation/ring-closure tandem reaction sequence. Using readily available building blocks, this strategy allows access to diversified optically pure morpholino monomers in good yields and anomeric ratios.
ISSN:2052-4110
2052-4110
DOI:10.1039/d2qo00400c