Synthesis and conformational analysis of pyran inter-halide analogues of ᴅ-talose

• Olivier Lessard,
• Mathilde Grosset-Magagne,
• Paul A. Johnson and
• Denis Giguère

Beilstein J. Org. Chem. 2024, 20, 2442–2454, doi:10.3762/bjoc.20.208

• axial substituent at C4 generally leads to a gt conformation [42][43], with some exceptions [24]. Bond distances, bond angles, torsion angles, and key interatomic distances are listed in Tables 1–4. It is important to point out that these results compare well with previous analysis of polyfluorinated

• carbohydrates [44][45]. The C–C bond lengths within the pyran rings of halogenated analogues are between 1.50 and 1.54 Å, which is similar to native talose (18, 1.52–1.53 Å) (Table 1, entries 1–4). However, all specified bond lengths within the pyran rings are shorter for halogenated analogues compared to α-ᴅ

Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose

• Danny Lainé,
• Vincent Denavit,
• Olivier Lessard,
• Laurie Carrier,
• Charles-Émile Fecteau,
• Paul A. Johnson and
• Denis Giguère

Beilstein J. Org. Chem. 2020, 16, 2880–2887, doi:10.3762/bjoc.16.237

• ; polyfluorinated carbohydrates; polyfluoroalditol analogues; Introduction The biological significance of carbohydrates includes, but are not limited to, immune regulation, infection, and cancer metastasis. Research in the field of molecular biology allowed the discovery of glycomimetics to study various

• were involved, among other things [5], in binding with UDP-Gal mutase [14], immunoglobulin [15][16], and glycogen phosphorylase [17]. The synthesis of complex polyfluorinated carbohydrates is challenging and new synthetic methods must be developed. Pioneering work by many groups brought significant