In 2022,Afari, Mark N. K.; Virta, Pasi; Lonnberg, Tuomas published an article in Organic & Biomolecular Chemistry. The title of the article was 《N-Methoxy-1,3-oxazinane nucleic acids (MOANAs) – a configurationally flexible backbone modification allows post-synthetic incorporation of base moieties》.Electric Literature of C9H10O2 The author mentioned the following in the article:
(2R,3S)-4-(Methoxyamino)butane-1,2,3-triol was converted into a protected phosphoramidite building block and incorporated into the middle of a short DNA oligonucleotide. O1 and O3 of the (2R,3S)-4-(methoxyamino)butane-1,2,3-triol were engaged in phosphodiester linkages, leaving O2 and the methoxyamino function available to form an N-methoxy-1,3-oxazinane ring through reaction with an aldehyde. In modified oligonucleotides thus obtained, the oxazinane ring formally replaces the furanose ring and the aldehyde, the base moiety of natural nucleosides. The feasibility of synthesizing base-modified oligonucleotides by this approach was demonstrated with several aromatic and aliphatic aldehydes featuring various functional groups. The experimental part of the paper was very detailed, including the reaction process of 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Electric Literature of C9H10O2)
2-(Benzyloxy)acetaldehyde(cas: 60656-87-3) is a non-natural aldehyde. It undergoes enantioselective Mukaiyama aldol reaction with silylketene acetal nucleophiles in the presence of C2-symmetric bis(oxazolinyl)pyridine Cu(II) complex (catalyst).Electric Literature of C9H10O2
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem