Carba-D,L-allal- and -D,L-galactal-derived vinyl &ITN&IT-nosyl aziridines as useful tools for the synthesis of 4-deoxy-4-(&ITN&IT-nosylamino)-2,3-unsaturated-5&ITa&IT-carbasugars

TETRAHEDRON

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Article

Di Bussolo, Valeria¹  Frau, Ileana^2,3  Favero, Lucilla²  Bordoni, Vittorio²  Crotti, Stefano^2,4  Barretta, Gloria Uccello¹  Balzano, Federica¹  Crotti, Paolo² 

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

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

[3] QuintilesIMS, Via Roma 10, I-20060 Milan, Italy

[4] Kedr Biopharma, Gallicano, Lucca, Italy

关键词: Vinyl aziridines;    4-(N-nosylamino)-carbasugars;    Carbaglycosylation;    Regioselectivity;   

DOI  :  10.1016/j.tet.2017.09.031

来源: Elsevier

【 摘 要 】

The novel carba-D,L-aIlal- and carba-D,L-galactal-derived vinyl N-nosyl aziridines were prepared and the regio- and stereoselective behavior in opening reactions with O- and N-nucleophiles examined. The carbaglycosylating ability of the novel aziridines, as deduced by the amount of 1,4-addition products (1,4-regioselectivity) obtained in the acid-catalyzed methanolysis taken as a model reaction, is similar or superior to that observed with the corresponding carba-D,L-allal- and -D,L-galactal-derived vinyl epoxides, respectively. In all 1,2- and 1,4-addition products obtained, a -(N-nosylamino) group is regio- and stereoselectively introduced at the C(4) carbon of a 1,2- or 2,3-unsaturated carbasugar, susceptible to further elaborations toward aminocyclitol derivatives. The stereoselective synthesis of the corresponding, enantiomerically pure carba-D,L-allal- and -D,L-galactal-derived vinyl N-acetyl aziridines is also described. (C) 2017 Elsevier Ltd. All rights reserved.

【 授权许可】

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