Diverse Synthesis of Natural Trehalosamines and Synthetic 1,1′‐Disaccharide Aminoglycosides

• Published in: Chembiochem : a European journal of chemical biology 2019-01, Vol.20 (2), p.287-294
• Main Authors: Lu, Yen‐Chu, Mondal, Soumik, Wang, Ching‐Chi, Lin, Chun‐Hung, Mong, Kwok‐Kong Tony
• Format: Article
• Language: English
• Subjects: Amino groups; Aminoglycosides; Configurations; Disaccharides; Glycosylation; Magnetic resonance spectroscopy; NMR spectroscopy; protecting groups; Synthesis; trimethylsilyl glycoside acceptors
• ISSN: 1439-4227; 1439-7633
• DOI: 10.1002/cbic.201800656

A general strategy for the diverse synthesis of ten disaccharide aminoglycosides, including natural 2‐trehalosamine (1), 3‐trehalosamine (2), 4‐trehalosamine (3), and neotrehalosyl 3,3′‐diamine (8) and synthetic aminoglycosides 4–7, 9, and 10, has been developed. The aminoglycoside compounds feature different anomeric configurations and numbers of amino groups. The key step for the synthesis was the glycosylation coupling of a stereodirecting donor with a configuration‐stable TMS glycoside acceptor. Either the donor or acceptor could be substituted with an azido group. The aminoglycosides prepared in the present study were characterized by 1D and 2D NMR spectroscopy. Short and sweet: A general strategy for the synthesis of ten disaccharide aminoglycosides, including three natural trehalosamines, neotrehalosyl 3,3′‐diamine, and six synthetic aminoglycosides, is developed. The aminoglycoside compounds have different anomeric configurations and numbers of amino groups. Glycosylation coupling of a stereodirecting donor with a configuration‐stable TMS glycoside acceptor is the key step.