A novel strategy towards the synthesis of orthogonally functionalised 4-aminoglycosides.
A tethered nucleophilic substitution strategy for the stereoselective introduction of axially oriented amino functions on suitably protected gluco- and mannopyranosides is presented. The obtained oxazine is a versatile building block, which after some manipulation, could be used in the construction of highly functionalised oligosaccharides.
van den Bos
Leendert J
LJ
Leiden Institute of Chemistry, Leiden University, Gorlaeus Laboratories, PO Box 9502, 2300 RA Leiden, The Netherlands.
Codée
Jeroen D C
JD
van Boom
Jacques H
JH
Overkleeft
Herman S
HS
van der Marel
Gijsbert A
GA
D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000617:Aminoglycosides