959409-89-3Relevant academic research and scientific papers
D-Glucosamine trimethylene dithioacetal derivatives: Formation of six- and seven-membered ring amino carbasugars. Synthesis of (-)-calystegine B 3
Chen, Yue-Lei,Redlich, Hartmut,Bergander, Klaus,Froehlich, Roland
, p. 3330 - 3339 (2008/09/21)
By virtue of carefully chosen protecting groups, d-glucosamine trimethylene dithioacetal derivatives were successfully oxidized to the corresponding 6-aldehydes. This methodology reverses the donor and acceptor position on a normal open chain sugar and changes the relative position of the N-substituent. From the 6-aldehydes, heptose epoxide derivatives were prepared by a Corey-Chaykovsky reaction, and cyclized by the Corey-Seebach method. Depending on the designed protecting groups, the orthogonally protected six- and seven-membered ring amino carbasugars can be produced selectively and efficiently. (-)-Calystegine B3 was synthesized from one of those products with high yield. This is the first anionic cyclization pathway to calystegine type structures. This journal is The Royal Society of Chemistry.
