Homo-C-nucleoside analogs II. Synthesis and anomeric configuration of 4- (2,5-anhydro-D-glucopentitol-1-yl)-2-phenyl-2H-1,2,3-triazole

Article abstract of DOI:10.1080/07328319808004234

Treatment of 4-(D-gluco-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole (1) with p-toluenesulfonyl chloride in pyridine solution, afforded the homo-C- nucleoside analog, 4-(2,5-anhydro-D-gluco-pentitol-1-yl)-2-phenyl-2H-1,2,3- triazole (2) as well as its partial p-toluenesulfonyl derivative (3). 4-(5- Chloro-5-deoxy-D-gluco-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole (8), was isolated as a byproduct from the reaction. The structure and anomeric configuration of 2 was determined by acylation, ¹H, ¹³C NMR, and NOE, spectroscopy as well as mass spectrometry.

Full text of DOI:10.1080/07328319808004234

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Homo-C-Nucleoside Analogs II. Synthesis
and Anomeric Configuration of 4-(2,5-
Anhydro-D-Gluco-PEntitol-1-YL)-2-
Phenyl2H-1,2,3-Triazole
Mohammed A. E. Sallam a & Leroy B. Townsend b
a Department of Chemistry, Faculty of Science , Alexandria
University , Alexandria, Egypt
b Department of Medicinal Chemistry , School of Pharmacy,
University of Michigan , Ann Arbor, MI, 48109, USA
Published online: 21 Aug 2006.
To cite this article: Mohammed A. E. Sallam & Leroy B. Townsend (1998) Homo-C-Nucleoside Analogs
II. Synthesis and Anomeric Configuration of 4-(2,5-Anhydro-D-Gluco-PEntitol-1-YL)-2-Phenyl2H-1,2,3-
Triazole , Nucleosides and Nucleotides, 17:7, 1215-1229, DOI: 10.1080/07328319808004234
To link to this article: http://dx.doi.org/10.1080/07328319808004234
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