Stereoselective synthesis of d-galactal-derived N-ethoxycarbonyl aziridine, as a new, improved synthetic protocol to glycal-derived N-activated vinyl aziridines

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• 作者：Salvatore Princiotto^a ; ^{elpincio89@gmail.com} ; Valeria Di Bussolo^b ; ^{valeria.dibussolo@unipi.it} ; Vittorio Bordoni^a ; Lucilla Favero^a ; Stefano Crotti^a ; ¹ ; Gloria Uccello Barretta^b ; Federica Balzano^b ; Paolo Crotti^a ; ^{paolo.crotti@farm.unipi.it}
• 关键词：Vinyl aziridines ; Glycals ; Glycosylation ; 4-N-(protected)-O-glycosides ; Stereoselectivity
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：16 February 2017
• 年：2017
• 卷：73
• 期：7
• 页码：829-837
• 全文大小：980 K
• 卷排序：73

文摘

A new protocol for the synthesis of d-galactal-derived N-ethoxycarbonyl vinyl aziridine 1β-CO2Et, starting from tri-O-acetyl-d-glucal, is described. The new protocol constitutes a simple and fast access, with a satisfactory overall yield (5 steps, 36%), to a d-galactal-derived vinyl aziridine with a clear improvement compared with the previously described procedure leading to the structurally related N-nosyl aziridine 1β-Ns which, starting from the same precursor, proceeded through 13 steps with a low, decidedly unsatisfactory, overall yield (3%).