Abstract
[reaction: see text]. Syntheses of cyclic phosphonate (phostone) analogues of carbohydrates containing a phosphorus atom at the anomeric position are described. The ring-closing metathesis reaction of mixed allylic phenyl esters of allylphosphonic acid 2 and 22 generates the six-membered allylic phosphonates 3 and 23 in excellent yields. Introduction of the polyhydroxy functionality in these cyclic phosphonates provides facile entry into an array of phostone sugar analogues.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Carbohydrates / chemical synthesis*
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Crystallography, X-Ray
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Cyclization
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Heterocyclic Compounds, 1-Ring / chemical synthesis*
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Hexoses / chemical synthesis
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Molecular Structure
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Organophosphonates / chemical synthesis*
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Phosphorus Acids / chemical synthesis*
Substances
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Carbohydrates
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Heterocyclic Compounds, 1-Ring
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Hexoses
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Organophosphonates
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Phosphorus Acids