Abstract
AbstractA number of new glycosyl donors, O‐(1‐phenyl‐1H‐tetrazol‐5‐yl) glycosides, are prepared from the corresponding hemiacetals, commercially available 5‐chloro‐1‐phenyl‐1H‐tetrazole (2), and tetrabutylammonium fluoride (Bu4NF) in either THF or DMF. The mild reaction conditions are compatible with a variety of protecting groups. The glycosyl donors are treated with hydrogen fluoride‐pyridine complex (HF·py) to rapidly provide glycosyl fluorides in good‐to‐excellent yields, apparently by a (single or double) SN2 mechanism as studied by both 1H‐ and 19F‐NMR spectroscopy. Under acidic conditions, glycosyl fluorides equilibrate partially or completely, equilibration requiring a large excess of HF · py.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.