Pyrrolidine Sugars. Synthesis of 4'-Acetamidoadenosine and Other Derivatives of 4-Amino-4-deoxy-D-ribose¹

Synthesis of some monocyclic-N-acetyl 4′-aza-D-nucleosides

“…For example the 1 H NMR spectrum of 6 indicated a doublet at 6.28 with a J value of 6.04 Hz supporting the assignment of configuration [25] for H 1' . Further the J values for H 1 of 12 were also in agreement with that of its L-isomer [21].…”

“…The 1 H NMR analysis of the products indicated that the structure of slower product as 23 and the structure of the faster product as 24. 1- [3,1,3, (25). (25) ,6.21;N,14.38.…”

The synthesis of piperidine nucleoside analogs—a comparison of several methods to access the introduction of nucleobases

“…4e7 Sugar-modified nucleosides represent an important group of antimetabolites that exhibit a variety of biological properties. First, azasugar nucleoside analog 3 was reported by Reist et al 8 The ring nitrogen atom of this compound was acylated otherwise it would undergo spontaneous hydrolysis. Owing to the instability of iminonucleosides, most of the research has been focused on nonglycosidic or aza-C-nucleosides.…”

The Synthesis and Conformation of Dihydroxypiperidinyl Derivates of Nucleobases as Novel Iminosugar Nucleoside Analogs

“…[3] The isoxazolidine derivative 3 was claimed to be an efficient inhibitor of HIV reverse transcriptase with low levels of cytotoxicity. [4] To the best of our knowledge, synthesis of the first azasugar nucleoside analog 4 was reported by Reist et al [5] The ring nitrogen atom of this compound was acylated to prevent it from spontaneous hydrolysis. Owing to the instability of iminonucleosides, most of the research has been focused on non-glycosidic or aza-C-nucleosides.…”