A short and scalable route to orthogonally O-protected 2-deoxystreptamine.
A seven-step synthesis of orthogonally O-protected 2-deoxy-streptamine has been developed from readily available neomycin, with an overall yield of 28%. Key chemical transformations include a chemoselective glycosidic bond hydrolysis and two regioselective protective group manipulations involving acetylation and deacetylation. The synthetic route is amenable to scale-up for the production of multigram quantities of enantiopure and orthogonally O-protected 2-deoxystreptamine, a versatile scaffold for the generation of libraries of RNA-targeting ligands.
van den Broek
Sebastiaan Bas A M W
SB
Chiralix B.V., P.O. Box 31070, 6503 CB Nijmegen, The Netherlands.
Gruijters
Bas W T
BW
Rutjes
Floris P J T
FP
van Delft
Floris L
FL
Blaauw
Richard H
RH
D002625:Chemistry, Organic / Q000379:methods*; D006595:Hexosamines / Q000138:chemical synthesis / Q000737:chemistry; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D009355:Neomycin / Q000737:chemistry
D006595:Hexosamines; D009355:Neomycin; C007265:2-deoxystreptamine