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%).

Stereoselective synthesis of D-galactal-derived N-ethoxycarbonyl aziridine, as a new, improved synthetic protocol to glycal-derived N-activated vinyl aziridines / S. Princiotto, V. Di Bussolo, V. Bordoni, L. Favero, S. Crotti, G. Uccello Barretta, F. Balzano, P. Crotti. - In: TETRAHEDRON. - ISSN 0040-4020. - 73:7(2017 Feb 16), pp. 829-837. [10.1016/j.tet.2016.12.047]

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

S. Princiotto
Primo
;
2017

Abstract

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%).
4-N-(protected)-O-glycosides; Glycals; Glycosylation; Stereoselectivity; Vinyl aziridines
Settore CHIM/06 - Chimica Organica
16-feb-2017
https://www.sciencedirect.com/science/article/abs/pii/S0040402016313345
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/969443
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