Synthesis and Reactions of 1,4‐Anhydrogalactopyranose and 1,4‐Anhydroarabinose – Steric and Electronic Limitations

2005/11/01 by Toshiki Nokami, Daniel B. Werz, Daniel B. Werz +2 · 1 citation
Chemistry · Biochemistry, Genetics and Molecular Biology · Nursing · #Carbohydrate Chemistry and Synthesis #Glycosylation and Glycoproteins Research #Microbial Metabolites in Food Biotechnology

paper · doi:10.1002/hlca.200590224

Abstract

Abstract Scope and limitations of 1,4‐anhydro sugars as precursors of glycofuranosyl building blocks are described. The experiments revealed that the choice of the substituents is very important for an efficient preparation as well as a successful ring‐opening reaction of 1,4‐anhydro sugars. DFT Calculations suggest that selective protonation of 1,4‐anhydro sugars is the key to the selective ring opening in order to afford only furanosides.

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