312538-75-3Relevant academic research and scientific papers
Strategies for stereocontrol at C1 or C2 in syntheses of α-glucosaminides
Fraser-Reid, Bert,Anilkumar,Nair, Latha G.,Olsson, Lars,Martin, Mercedes Garcia,Daniels, Jacquitta K.
, p. 255 - 262 (2000)
The C1 and C2 stereocenters of α-glucosaminides can be prepared by establishing the stereocenters in either order. For the former, a C2-azido glucosyl donor is prepared first, and the restraining effect of a 4,6-O-benzylidene ring is used to induce α-coupling. For the latter, the C1 linkage is prepared first by use of an n-pentenyl-manno-1,2-orthoester donor which ensures (a) clean α-coupling and (b) a convenient C2-ester. The C2-ester is replaced with a triflate leaving group, and nucleophilic displacement is effected by use of a hypervalent silicon azide.
α-Glucosaminide synthesis: Exercising stereocontrol at C1 or C2 via torsional effects or DeShong nucleophiles
Anilkumar,Nair, Latha G.,Olsson, Lars,Daniels, Jacquitta K.,Fraser-Reid, Bert
, p. 7605 - 7608 (2007/10/03)
The synthesis of α-glucosaminides may be carried out by installing synthons for the cis-related C1 and C2 functionalities in either order. When the C2 azide is installed first, α-glycosidation can be induced by using a 4,6-O-benzylidene ring to provide torsional control of anomeric selectivity. In the alternative option, the C1 linkage can be established by use of an n-pentenyl-manno-1,2-orthoester, the C2-oxygen of the resulting α-mannoside being replaced with inversion by use of DeShong's hypervalent silicon azide. (C) 2000 Elsevier Science Ltd.
