Synthesis and glycosidase inhibitory activity of new hexa- substituted C8-glycomimetics

• Olivia Andriuzzi,
• Christine Gravier-Pelletier,
• Gildas Bertho,
• Thierry Prangé and
• Yves Le Merrer

Beilstein J. Org. Chem. 2005, 1, No. 12, doi:10.1186/1860-5397-1-12

• H2 (proS), H8 and H7 (proS) indicate a pseudo-equatorial position of protons H2 (proS) and H7 (proS). NOE measurements and finally Molecular Dynamic calculations using Insight II software (Biosym Technologies, San Diego, CA) allowed to deduce the structure of 11 (Figure 4). Prochiral H2 (proS) and H7

• protons (in bold) of the upper face of the C8 ring. Prochiral 1H are labelled pR or pS. X-ray structure of epoxide 7 (upper) and sulfate 9 (down) solved using SHELXS and anisotropically refined using SHELXL programs [38]. Reagents and conditions: (a) OsO4, NMO, tBuOH, rt; (b) TFA, H2O, rt. Reagents and