(<em>1R</em>,<em>4S</em>,<em>5S</em>)-5-((3-Hydroxypropyl)amino)-4-((1-methyl-1<em>H</em>-tetrazol-5-yl)thio)cyclopent-2-en-1-ol

Abstract

Using environmentally friendly conditions, the nucleophilic ring-opening reaction of 6-azabicyclo[3.1.0]hex-3-en-2-ol with 1-methyl-1H-tetrazole-5-thiol provided a novel thiol-incorporated aminocyclopentitol, (1R,4S,5S)-5-((3-hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio)cyclopent-2-en-1-ol, in excellent yield (95%). The newly synthesized compound was analyzed and characterized via 1H, 13C-NMR, HSQC, and mass spectral data.

Keywords

• aminocyclopentitol
• bicyclic aziridine
• water chemistry
• nucleophilic substitution