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- W2093317606 abstract "Abstract Derivatives of l -iduronic acid were prepared by epimerisation of d -glucuronic acid derivatives that were constrained to adopt a conformation having C-6 in an axial position, so that the l -iduronic acid derivatives would be thermodynamically more stable. Methyl 3,5- O -benzylidene-1,2- O -isopropylidene-β- l -idofuranuronate was conveniently obtained in 23% yield by crystallisation from the epimerising mixture and was characterised either by reduction to the corresponding alcohol or by catalytic hydrogenation followed by spontaneous cyclisation to give 1,2- O -isopropylidene-β- l -idofuranurono-6,3-lactone. A synthesis of methyl 3,5- O -benzylidene-1,2- O -isopropylidene-α- d -glucofuranuronate in two steps from d -glucofuranurono-6,3-lactone was devised. Other candidates for epimerisation, including other esters, amides, and nitriles, were also examined. In all cases, the yields were reduced by competing decomposition, probably involving β-elimination." @default.
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- W2093317606 date "1982-10-01" @default.
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- W2093317606 title "Synthesis of l-iduronic acid derivatives by epimerisation of anancomeric d-glucuronic acid analogues" @default.
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- W2093317606 doi "https://doi.org/10.1016/s0008-6215(00)81890-x" @default.
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