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Synthesis of some monocyclic‐ N ‐acetyl 4′‐aza‐D‐nucleosides
Author(s) -
Varaprasad Chamakura V. N. S.,
Ramasamy Kanda S.,
Hong Zhi
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430212
Subject(s) - chemistry , thymine , nitrogen atom , ring (chemistry) , nucleoside , condensation , ammonia , stereochemistry , nitrogen , oxygen atom , sugar , medicinal chemistry , organic chemistry , dna , molecule , biochemistry , physics , thermodynamics
1,2,3,5‐Tetra‐ O ‐acetyl‐4‐deoxy‐4‐(acetamido)‐β‐D‐ribofuranose 5 was prepared from L‐lyxose, which on condensation with silylated nucleoside bases gave the corresponding protected 4′‐azanucleosides. The protecting groups were removed using methanolic ammonia to afford the N ‐acetyl‐4′‐azanucleosides, wherein the sugar ring oxygen is replaced with a substituted nitrogen atom, in good yields. Further, the 1‐(4‐deoxy‐4‐acetamido‐β‐D‐ribofuranosyl)thymine 16 was transformed to the corresponding 2′‐deoxy, 2′,3′‐dideoxy derivatives. The stereochemical assignments of the synthesized nucleosides were established based on NMR and X‐ray studies.