N-糖基-N'-酰氨基硫脲及其环合产物的合成

Synthesis of N-Glycosyl-N'-amido Thioureas and Their Related Heterocyclic Compounds

以L-α-氨基酸为起始原料,经酯化、氨基保护、肼解制得N-对甲苯磺酰基-L-α-氨基酸酰肼2,再与糖基异硫氰酸酯3～5反应,得到9种新型N-糖基-N'-酰氨基硫脲6～8,然后在Hg(OAc)2/EtOH条件下关环,合成了一系列新的2-对甲苯磺酰氨基烃基-5-糖氨基-1,3,4-噁二唑类化合物9～11.所有新化合物的结构均经IR,1H NMR,MS谱和元素分析确证.

The starting material L-α-amino acids were converted into N-p-toluenesulfonyl-L-α-amino acid hydrazides 2 through following steps, esterification, amino protection and hydrazinolysis. The reaction of 2 with glycosyl isothiocyanates 3-5 gave the novel compounds, N-glycosyl-N＇-amido thioureas 6-8. The compounds 6-8 were cyclized under the system of Hg（OAc）2/EtOH to afford a series of new compounds, 2p-toluenesulfonylaminoalkyl-5-glycosylarnino-1,3,4-oxadiazoles 9-11. The structures of the new compounds were confirmed by IR, ^1H NMR, MS spectra and elemental analysis.