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

TETRAHEDRON

卷:73

Article

Princiotto, Salvatore¹  Di Bussolo, Valeria²  Bordoni, Vittorio¹  Favero, Lucilla¹  Crotti, Stefano¹  Barretta, Gloria Uccello²  Balzano, Federica²  Crotti, Paolo¹ 

[1] Univ Pisa, Dipartimento Farm, Via Bonanno 33, I-56126 Pisa, Italy

[2] Univ Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 3, I-56124 Pisa, Italy

关键词: Vinyl aziridines;    Glycals;    Glycosylation;    4-N-(protected)-O-glycosides;    Stereoselectivity;   

DOI  :  10.1016/j.tet.2016.12.047

来源: Elsevier

【 摘 要 】

A new protocol for the synthesis of D-galactal-derived N-ethoxycarbonyl vinyl aziridine 1 beta-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 1 beta-Ns which, starting from the same precursor, proceeded through 13 steps with a low, decidedly unsatisfactory, overall yield (3%). (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

Free