82886-80-4Relevant academic research and scientific papers
Di- and Polyamino Sugars, XXX. - Reaction of a 2,3-Anhydro Sugar with an 6-Amino Sugar, Synthesis and Reactions of a N-epimino Sugar
Spohr, Ulrike,Meyer zu Reckendorf, Wolfgang
, p. 1375 - 1383 (2007/10/02)
The 2,3-epoxide 1 could stereoselectively be opened by the 6-amino sugar 2 to form the secondary amine 3 which was selectively acylated at C-2 of the altro-component.Tosylation of 3 led via the tosylate 9 to the aziridine 10 which could also be synthesized from the epimino sugar 13 and the epoxide 5.Under these tosylating conditions ring-opening of the aziridine 10 largely took place to give the 2-chloro-altro-compound 12.Contrary to this trans diaxial ring-opening the reaction of 10 with NH4Cl in boiling dimethylformamide preponderantly yielded the trans-diequatorial product 16 with gluco-configuration of the pyranose.
