Stereoselective synthesis of d-galactal-derived N-ethoxycarbonyl aziridine, as a new, improved synthetic protocol to glycal-derived N-activated vinyl aziridines. Issue 7 (16th February 2017)

• Record Type: Journal Article
• Authors: Princiotto, Salvatore; Di Bussolo, Valeria; Bordoni, Vittorio; Favero, Lucilla; Crotti, Stefano; Uccello Barretta, Gloria; Balzano, Federica; Crotti, Paolo
• Is Part Of: Tetrahedron. Volume 73:Issue 7(2017)
• Page Start: 829
• Page End: 837
• Publication Date: 2017-02-16
• Subjects: Vinyl aziridines -- Glycals -- Glycosylation -- 4-N-(protected)-O-glycosides -- Stereoselectivity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.12.047
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A new protocol for the synthesis ofd -galactal-derived N -ethoxycarbonyl vinyl aziridine1β-CO 2 Et, 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 ad -galactal-derived vinyl aziridine with a clear improvement compared with the previously described procedure leading to the structurally related N -nosyl aziridine1β-Ns which, starting from the same precursor, proceeded through 13 steps with a low, decidedly unsatisfactory, overall yield (3%). Graphical abstract: