Stereoselective synthesis of C-glycosylphosphonates from their ketols. Reconsideration of an abandoned route |
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| Institution: | 1. Medicinal Chemistry Laboratory, GVK Biosciences Pvt. Ltd., Plot No 28, IDA Nacharam, Hyderabad, 500076 Telangana, India;2. Department of Chemistry, Jawaharlal Nehru Technological University, Hyderabad, 500085 Telangana, India;1. Institut Pasteur, Unité de Chimie et Biocatalyse, 28 rue du Dr Roux, 75724 Paris cedex 15, France;2. CNRS, UMR3523, Paris, France;3. Université Paris Descartes, Sorbonne Paris Cité, Paris, France |
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| Abstract: | Isosteric phosphonate analogues of glycosyl 1-phosphates have been obtained by addition of LiCH2P(O)(OMe)2 to glyconolactones followed by Et3SiH–TMSOTf reductive dehydroxylation of the resultant ketols. The compounds prepared include four β-linked pyranose derivatives (d-galacto, 2-azido-2-deoxy-d-galacto, d-gluco, d-manno) and one β-linked furanose derivative (d-manno). In the latter case the ketol was activated as its 2-acetate. In agreement with an observation in another laboratory, the dehydroxylation of a model ketol phosphonate failed with the use of Et3SiH–BF3·Et2O. |
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