Syntheses of 6-Guanidino-hexoses and 5-Guanidino-pentoses

Abstract

Guanidinations of primary amines were performed with 3,5-dimethylpyrazolylformamidinium nitrate. 6-Deoxy-6-guanidino derivatives of unprotected N-acetyl-glucosamine and of glucosamine were prepared, with both products existing as pyranoses. In the pentose series, 5-deoxy-5-guanidinio-D-xylose nitrate (17) and -D-arabinose nitrate (22) were synthesized. For both compounds, besides some α-D-xylo-pyranose and β-D-arabino-pyranose, mainly the furanoses are found.