700360-94-7Relevant articles and documents
Synthesis of a protected enantiomerically pure 2-deoxystreptamine derivative from D-allylglycine
Busscher, Guuske F.,Rutjes, Floris P.J.T.,Van Delft, Floris L.
, p. 3629 - 3632 (2007/10/03)
A diastereoselective synthetic route from D-allylglycine to the enantiopure (protected) 2-deoxystreptamine derivative 14 is presented. Key steps involve two consecutive chain extensions - with crucial stereodirective roles for the amino protective groups, ring closure by olefin metathesis, face selective dihydroxylation, cyclic sulfate formation and finally opening with azide. The resulting 2-deoxystreptamine derivative is ideally protected for the preparation of 4,5- or 4,6-linked aminoglycoside antibiotics.