133497-13-9Relevant academic research and scientific papers
Artificial Deoxy Glycosides of Anthracyclines
Klaffke, Werner,Pudlo, Peter,Springer, Dirk,Thiem, Joachim
, p. 509 - 512 (2007/10/02)
In Lewis acid mediated allylic rearrangement reactions of L-rhamnal (1) and L-fucal (2) with daunomycinon (6) 2'-deoxyhex-2'-enopyranosides have been obtained exclusively.Furthermore, glycals 1 and 4 have been treated with the glycosyl acceptors 6, 7, and 9 and N-iodosuccinimide (NIS) to produce the corresponding α-configurated 2'-deoxy-2'-iodo glycosides.Among these, 16 represents a bis(glycoside) with both benzylic aglycon positions substituted.In none of the above cases has a substatial amount of β-glycoside been detected.Attempts to convert ε-isorhodomycinon (8) into a glycoside on a preparative scale, under Lewis acid conditions have been unsuccesful.However, the α-glycoside 13 has been obtained by the Helferich method.
