N‐Glykoside und Glykamine von Cyclopentylamin, 1.2.3.4‐Tetrahydro‐1‐naphthylamin und 5α‐Cholestan‐3β‐amin

Abstract

Von Cyclopentylamin werden die Galactosyl-, Glucosyl-, Mannosyl-und Lactosyl-N-Glykoside, von den beiden anderen Titelverbindungen die Galactosyl-und Glucosyl-N-Glykoside beschrieben. Alle N-Glykoside werden rnit Cyanoborhydrid zu den zugehorigen Glykaminen reduziert. N-Glycosides and Glycamines of Cyclopentylamine, 1,2,3,4-Tetrahydro-l-naphthylamine and 5a-CholestandfLamineThe galactosyl-, mannosyl-and lactosyl-N-glycosides of cyclopentylamine and the galactosyl-and glucosyl-N-glycosides of the other two title compounds are described. All N-glycosides are reduced by cyanoborohydride to the corresponding glycamines.Um den EinfluB des glykosidischen Sauerstoffs an C-3 der Glycyrrhizinsaure auf ihren suRen Geschmack kennen zu lernen, sollten von ihr N-Glykoside synthetisiert werden*). Wohl lief eine Reaktion zwischen der 3-Aminoglycyrrhetinsaure und Aldosen ab, doch gelang keine Isolierung der N-Glykoside

Synthesis of Potential Early-Stage Intermediates in the Biosynthesis of FR900482 and Mitomycin C

“…In practice, condensation of N -Cbz- d -glucosamine ( 17 )17 and AHBA18 under Brønsted-acid catalysis afforded N -glycoside 18 exclusively in the β-configuration (Scheme 2). Subsequent cleavage of the N -Cbz moiety using catalytic hydrogenolysis with palladium(II) oxide cleanly provided the requisite amino acid 1 19. Putative biosynthetic intermediate 2 was prepared in a two-step, one-flask N -glycosylation/reductive amination reaction sequence enlisting N -Cbz- d -glucosamine ( 17 ) and AHBA•HCl in the presence of sodium cyanoborohydride to provide amine 19 20.…”

“…Subsequent cleavage of the N-Cbz moiety using catalytic hydrogenolysis with palladium(II) oxide cleanly provided the requisite amino acid 1. 19 Putative biosynthetic intermediate 2 was prepared in a two-step, one-flask N-glycosylation/reductive amination reaction sequence enlisting N-Cbz-D-glucosamine (17) and AHBA•HCl in the presence of sodium cyanoborohydride to provide amine 19. 20 Unmasking the amine functionality using catalytic hydrogenolysis provided amino acid 2 in a fashion analogous to that applied to the preparation of amine 1.…”