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We describe a new protocol for the challenging differentiation of the position 2 ′ and 4 ′ of l-iduronyl moieties located at the nonreducing end of various disaccharide building blocks. This methodology is based on the introduction of a 2 ′ ,4 ′ -O-p-methoxybenzylidene group, followed by a totally regioselective reductive opening of this acetal by the PhBCl 2 ...
Methyl 1,2,4-tri-O-acetyl-3-O-benzyl-l-idopyranuronate 6β/6α, prepared from methyl 3-O-benzyl-l-iduronate (4), is a key synthon in heparin/heparan sulfate synthesis. The 1 H and 13 C NMR spectra of the furanose-pyranose mixture of 4, after dissolution and equilibration in d 4 -methanol, were fully assigned allowing to expect that 4 could crystallise in the β-pyranose form...
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