Synthesis and Conformational Analysis of Pyran Interhalide Analogues of Galactose, Mannose, Talose, and Glucose

There is growing interest in the preparation of multivicinal interhalide molecules. Herein, we described the synthesis of several pyran interhalide analogues of d-galactose, d-mannose, d-talose, and d-glucose. A robust and simple halogeno-divergent strategy provided pyran-bearing multivicinal interhalide stereocenters. However, a different strategy was implemented for the synthesis of glucose interhalides. The solid-state conformational analysis of some interhalide analogues showed differences in the deviation of the intra-annular torsion angles. Moreover, we observed the shortest F⋅⋅⋅I halogen bonding (XB) involving Csp3-bound I and F atoms.