Synthesis of 1,2,3-triazole and 1,2,3,4-tetrazole-fused glycosides and nucleosides by an intramolecular 1,3-dipolar cycloaddition reaction.
Various 1,2,3-triazole and 1,2,3,4-tetrazole fused multi-cyclic compounds were synthesized from carbohydrate derived azido-alkyne and azido-cyanide substrates. The acid sensitive 1,2-O-isopropylidene group of the furanosyl sugar was utilized for diversification to glycosides and nucleosides under Fischer glycosidation and Vorbruggen's conditions, respectively.
Anegundi
Ramakrishna I
RI
Division of Organic Chemistry, National Chemical Laboratory, Pune 411 008, India.
Puranik
Vedavati G
VG
Hotha
Srinivas
S
D000480:Alkynes / Q000737:chemistry; D003486:Cyanides / Q000737:chemistry; D003500:Cyclization; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013777:Tetrazoles / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
D000480:Alkynes; D003486:Cyanides; D006027:Glycosides; D009705:Nucleosides; D013777:Tetrazoles; D014230:Triazoles