Homo-C-Nucleoside Analogs†

For part I see ref. 1.

II. Synthesis and Anomeric Configuration of 4-(2,5-Anhydro-D-Gluco-PEntitol-1-YL)-2-Phenyl2H-1,2,3-Triazole††

For a preliminary report see ref. 2.

Abstract

Treatment of 4-(D-gluco-pentitol-l-y1)-2-pheny1–2H-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.

For part I see ref. 1.

For a preliminary report see ref. 2.

Notes

For part I see ref. 1.

For a preliminary report see ref. 2.