A short and highly efficient synthesis of L-ristosamine and L-epi-daunosamine glycosides.
A highly efficient synthesis of L-ristosamine and L-epi-daunosamine glycosides via BF(3)·OEt(2) promoted tandem hydroamination/glycosylation of 3,4-di-O-acetyl-6-deoxy-L-glucal and L-galactal has been developed. The new method proceeds in a completely stereocontrolled manner within a short reaction time. Preparation of a library of L-ristosamine and L-epi-daunosamine glycosides with potential biochemical applications, by varying each component, exemplified the generality of the reaction.
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.
Feiqing
F
Ding
Ronny
R
William
Fei
F
Wang
Jimei
J
Ma
Li
L
Ji
Xue-Wei
XW
Liu
D020650:Combinatorial Chemistry Techniques; D005690:Galactose / Q000031:analogs & derivatives / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006595:Hexosamines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D006027:Glycosides; D006595:Hexosamines; C007217:daunosamine; C002038:galactal; C010783:ristosamine; D005690:Galactose