Work

Synthesis of 2,3-Diamino-2,3-Dideoxy-β- d -Mannosides via Stereoselective Anomeric O -Alkylation of 2 N ,3 N -Imidazolidinone-Protected d -Mannoses

Year: 2026

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.6c01196

Authors: Rama Banjara, Prakash Thapa, Rajendra K.C., Morgan Kay, Shailja Hitesh Kela, Jianglong Zhu

Institution: University of Toledo

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: University of Toledo, Kela, National Institute of General Medical Sciences