944544-02-9Relevant articles and documents
Sugar-derived aziridines: Functionalization via lithiation of the aziridine ring
Bisseret, Philippe,Bouix-Peter, Claire,Jacques, Olivier,Henriot, Stephanie,Eustache, Jacques
, p. 1181 - 1182 (1999)
(Matrix Presented) Stereoselective preparation of a new arabinose-derived aziridine and functionalization of the corresponding N-BH3 complex are described. Regio-and stereoselective aspects are discussed.
A versatile approach to pyrrolidine azasugars and homoazasugars based on a highly diastereoselective reductive benzyloxymethylation of protected tartarimide
Zhou, Xiang,Liu, Wen-Jun,Ye, Jian-Liang,Huang, Pei-Qiang
, p. 6346 - 6357 (2008/02/05)
A highly diastereoselective synthesis of enantio-enriched all trans-3,4-dibenzyloxyl-5-benzyloxymethyl-2-pyrrolidinone 13a was developed based on SmI2-mediated benzyloxymethylation of O,O′-dibenzyltartarimide. The versatility of 13a and its antipode as the key building blocks for the asymmetric synthesis of pyrrolidine azasugars and homoazasugars has been demonstrated by elaborating them into naturally occurring DAB 1 (1), LAB 1 (2), N-hydroxyethyl-DAB 1 (4), 6-deoxy-DMDP 7, and 5-epi-radicamine B 36 as well as the reductive ring-opening product 35.