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

ABSTRACT: 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.

SUBMITTER: Lessard O 

PROVIDER: S-EPMC12319363 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature