Synthesis and nuclear magnetic resonance studies of some N-acylated methyl 4-amino-4,6-dideoxy-α-<scp>D</scp>-mannopyranosides
作者:Lennart Kenne、Per Unger、Thomas Wehler
DOI:10.1039/p19880001183
日期:——
The methyl α-glycosides of 4-amino-4,6-dideoxy-D-mannopyranose (perosamine), N-acylated with either formic, acetic, or (S)-2,4-dihydroxybutanoic acid, have been synthesized. The 1H and 13C n.m.r. spectra of these substances and the parent, non-N-acylated glycoside, demonstrated how the chemical shifts are influenced by the N-acylation. The N-formyl derivative occurred in two conformations, s-cis and
已经合成了被甲酸,乙酸或(S)-2,4-二羟基丁酸N-酰化的4-氨基-4,6-二脱氧-D-甘露吡喃糖(过胺)的甲基α-糖苷。的1 H和13 C ^这些物质和亲本的NMR谱,非Ñ -acylated糖苷,演示了如何将化学位移是由影响Ñ酰化。所述Ñ发生在两种构象,仲-甲酰基衍生物的顺式和S-反,和它们之间的自由能屏障,86.9千焦摩尔-1,通过动态核磁共振谱定义。