新型β-氨基醇及其中间体的合成与波谱研究

由D-木糖出发，经过杂D-A 反应、Henry反应、合成了中间体(1αS，2αR， 3αS，4S，7E，9αR，10αR)-1，2∶9，10-O-二异丙叉基-3-硝甲基-5，6-二脱氧-7-烯-4-氧化-1，4∶7，10-二呋喃-4，8-吡喃糖（化合物1），再经催化氢化，立体选择性地得到了含高碳糖结构片断的β-氨基醇(1αS，2αR， 3αS，4S，7αS，8βR，9αR，10αR)-1，2∶9，10-O-二异丙叉基-3-氨甲基-5，6-二脱氧-4-氧化-1，4∶7，10-二呋喃-4，8-吡喃糖（化合物2）， 通过DEPT和¹H-¹H COSY，HMQC，HMBC等2D NMR 技术对化合物1的¹H和¹³C NMR数据进行了全归属和较详细的解析并探讨了其ESI-MS/MS质谱裂解规律. 同时得到化合物1的还原产物化合物2的¹H，¹³C NMR归属.

A New Higher Carbon Sugar-Derived Amino Alcohol and Its Intermediate: Synthesis and NMR Studies

An intermediate of higher carbon sugar-derived amino alcohol (1αS, 2αR, 3αS, 4S, 7E, 9αR, 10αR)-1, 2∶9, 10-di-O-isopropylidene-3-nitromethyl-5, 6-dideoxy-dec-7-enos-4-ulose-1, 4∶7, 10-difuranose-4, 8-pyranose) (compound 1) was synthesized from D-xylose using hetero-Diels-Alder addition followed by Henry reaction. Compound 2 (1αS, 2αR, 3αS, 4S, 7αS, 8βR, 9αR, 10αR)-1, 2∶9, 10-di-O-isopropylidene-3-aminomethyl-5, 6-dideoxy-dec-4-ulose-1, 4∶7, 10-difuranose-4, 8-pyranose) was synthesized stereoselectively by catalytic hydrogenation of compound 1. Complete assignment of ¹H and ¹³C chemical shifts of compounds 1 and 2 was obtained by 2D NMR techniques, including ¹H-¹H COSY, HMQC and HMBC. ESI-MS/MS spectra of compound 1 were also measured to study its fragmentation behaviors. The structure of compound 2 was determined.