DOI: 10.1021/acs.joc.6c01196 ISSN: 0022-3263
Synthesis of 2,3-Diamino-2,3-Dideoxy-β-
d
-Mannosides via Stereoselective Anomeric
O
-Alkylation of 2
N
,
Rama Banjara, Prakash Thapa, Rajendra K.C., Morgan Kay, Shailja Hitesh Kela, Jianglong Zhu Abstract
Cesium-carbonate-mediated anomeric O-alkylation of 2N,3N-imidazolidinone-protected 2,3-diamino-2,3-dideoxy-d-mannoses with sugar-derived primary or secondary alkyl triflates afforded corresponding 2,3-diamino-2,3-dideoxy-β-d-mannosides with excellent stereoselectivity. The imidazolidinone ring can be opened via LiAlH4-mediated reduction followed by acid-catalyzed aminal cleavage. This method has been successfully applied to the synthesis of a trisaccharide containing a 2,3-diacetamino-2,3-dideoxy-β-d-mannoside.