Tetrahedron
Tetrahedron
5 years ago

Synthesis and properties of 2-deoxy-2-fluoromannosyl phosphate derivatives

Synthesis and properties of 2-deoxy-2-fluoromannosyl phosphate derivatives
2-Deoxy-2-fluoromannosyl phosphotriester and phosphodiester derivatives were synthesized and they were demonstrated to be more stable than the 2-OH compounds under acidic conditions. 2-Fluoro substituted analog of α-mannopyranosyl 1-phosphodiester 20 was found to be significantly stable at pH 1, where 2-OH compound 21 was gradually hydrolyzed. In addition, 2-F analogs of α-mannopyranosyl 1-phosphotriesters also was found to be stable under both Brønsted and Lewis acidic conditions. These results strongly suggested that the 2-F substitution is useful for both the synthesis of mannosyl phosphodiester derivatives and improvement of their chemical stability.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017306348

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