Synthesis of L-daunosamine and L-ristosamine glycosides via photoinduced aziridination. Conversion to thioglycosides for use in glycosylation reactions.
Synthesis of L-daunosamine and L-ristosamine glycosides via photoinduced aziridination. Conversion to thioglycosides for use in glycosylation reactions.
复制标题
DOI：
10.1021/jo061167z
复制
发表时间：
2006-09
期刊：
影响因子：
--
通讯作者：
Matthew T. Mendlik;Peng Tao;C. Hadad;R. S. Coleman;T. Lowary
中科院分区：
文献类型：
--
作者：
Matthew T. Mendlik;Peng Tao;C. Hadad;R. S. Coleman;T. Lowary
报道了光诱导酰基硝基烯叠氮化在l -丹诺胺和l -里斯托胺苷合成中的应用。甲基4- o-叠氮羰基-2,3,6-三脱氧- l-己-2-烯吡喃苷的光化学反应，再加上叠氮啶的开孔，得到3-氨基-3- n -，4- o-羰基-2,3,6-三脱氧的氨基糖甲基糖苷前体。将这些前体转化为其巯基糖苷类似物，然后对氨基甲酸酯部分进行n -乙酰化，在某些情况下，使用Crich及其同事开发的1-苯磺酸基哌啶-三酸酐活化方法可以实现高产量和立体选择性糖基化。与n -碘琥珀酰亚胺和三氟酸银活化的糖基化也很成功，但这些反应的立体选择性一般较低。
Application of photoinduced acylnitrene aziridination to the syntheses of L-daunosamine and L-ristosamine glycosides is reported. Photoreaction of methyl 4-O-azidocarbonyl-2,3,6-trideoxy-L-hex-2-enopyranosides, followed by aziridine opening, leads to 3-amino-3-N-,4-O-carbonyl-2,3,6-trideoxy precursors to the aminosugar methyl glycosides. Conversion of these precursors to their thioglycoside analogues followed by N-acetylation of the carbamate moiety permits high yielding and, in some cases, stereoselective glycosylations using the 1-benzenesulfinylpiperidine-triflic anhydride activation method developed by Crich and co-workers. Glycosylations involving activation with N-iodosuccinimide and silver triflate were also successful, but the stereoselectivities of these reactions in general were lower.