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

## TL;DR

This paper describes the synthesis and structural analysis of halogen-containing sugar analogs, revealing unique halogen bonding interactions.

## Contribution

A new halogeno-divergent strategy for synthesizing pyran interhalide analogs and the discovery of the shortest F⋅⋅⋅I halogen bond.

## Key findings

- A robust halogeno-divergent strategy was developed for synthesizing pyran interhalide analogs of d-galactose, d-mannose, d-talose, and d-glucose.
- Solid-state conformational analysis revealed differences in intra-annular torsion angles among the interhalide analogs.
- The shortest F⋅⋅⋅I halogen bonding was observed involving Csp3-bound iodine and fluorine atoms.

## 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.

The synthesis and conformational analysis of pyran interhalides unveiled the shortest F⋅⋅⋅I halogen bonding involving Csp3‐bound I and F atoms.