Fully orthogonally protected 2-deoxystreptamine from kanamycin.
A fully orthogonally protected and enantiopure 2-deoxystreptamine derivative is prepared in a few straightforward steps from commercially available kanamycin. Resolution of a sterically hindered diacetate was effected by a Verenium esterase and was followed by a chemoselective Staudinger reduction-acylation protocol.
Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands.
M Waqar
MW
Aslam
Guuske F
GF
Busscher
David P
DP
Weiner
René
R
de Gelder
Floris P J T
FP
Rutjes
Floris L
FL
van Delft
D006595:Hexosamines / Q000737:chemistry; D007612:Kanamycin / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure
D006595:Hexosamines; D007612:Kanamycin; C007265:2-deoxystreptamine