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Convenient Synthesis of Nucleosides of 2‐Deoxy‐2‐nitro‐ D ‐galactose and N ‐Acetyl‐ D ‐galactosamine
Author(s) -
Winterfeld Gottfried A.,
Das Jagattaran,
Schmidt Richard R.
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200009)2000:17<3047::aid-ejoc3047>3.0.co;2-6
Subject(s) - chemistry , indazole , nitro , regioselectivity , imidazole , acetylation , stereochemistry , galactosamine , benzimidazole , benzotriazole , nucleoside , medicinal chemistry , galactose , organic chemistry , catalysis , biochemistry , alkyl , gene
A new method for the construction of nucleosides of 2‐deoxy‐2‐nitro‐ D ‐galactose and of N ‐acetyl‐ D ‐galactosamine based on addition reactions to 3,4,6‐tri‐ O ‐benzyl‐2‐nitro‐ D ‐galactal ( 1 ) is presented. The reaction of imidazole, benzimidazole, purine, N 6 ‐benzyladenine, indazole, benzotriazole, and pyridone with 1 under base activation afforded the corresponding β‐glycosides with a high degree of stereo‐ and regioselectivity. Reduction of the 2‐deoxy‐2‐nitro‐nucleosides 3 and 4 gave, after N ‐acetylation, the corresponding 2‐acetamido‐2‐deoxy‐nucleosides 9 and 10 . Complete deprotection of 9 was achieved with H 2 in the presence of Pd(OH) 2 /C and THF as solvent.