200712-58-9

Upstream product

• 200712-56-7 methyl(2-O-benzoyl-4,6-O-isopropylidene-3-O-methyl-α-L-idopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 1186009-53-9 methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-benzylidene-2,3-di-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside 
• 162610-20-0 methyl(4,6-O-isopropylidene-3-O-methyl-α-L-idopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 200712-57-8 methyl(4,6-O-isopropylidene-2,3-di-O-methyl-α-L-idopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 200712-60-3 (2S,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dimethoxy-tetrahydro-pyran-3-ol 
• 192505-56-9 methyl (benzyl 2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 200712-63-6 methyl (benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 200712-66-9 (benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-acetyl-2-O-benzyl-1-O-trichloroacetimidoyl-D-glucopyranose 
• 200712-62-5 (2R,3S,4S,5R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4,5-dimethoxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid 
• 200712-64-7 (benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-1,3,6-tri-O-acetyl-2-O-benzyl-D-glucopyranose 
• 200712-61-4 methyl (6-O-tert-butyldimethylsilyl-4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Short Synthesis of Idraparinux by Applying a 2-O-Methyl-4,6-O-arylmethylene Thioidoside as a 1,2-trans-α-Selective Glycosyl Donor

The fully O-sulfated, O-methylated, heparin-related anticoagulant pentasaccharide idraparinux was prepared by a new synthetic pathway in 38 steps using d-glucose and methyl α-d-glucopyranoside as starting materials, with 23 steps for the longest linear route. The l-idose-containing GH fragment was obtained by a short and straightforward synthesis whereby a 4,6-cyclic-acetal-protected l-idosyl thioglycoside bearing a C2-nonparticipating group was used as the α-selective glycosyl donor. The novel l-idose donor was prepared with high chemo- and stereoselectivity by hydroboration–oxidation-based C5 epimerization starting from an orthogonally protected α-thioglucoside. The assembly of the pentasaccharide backbone was achieved by an F+GH and DE+FGH coupling sequence with full stereoselectivity in each glycosylation step.

Efficient synthesis of Idraparinux, the anticoagulant pentasaccharide

An efficient [DEF+GH] route was developed to the synthesis of Idraparinux, which is a fully O-sulfated, O-methylated mimic of the unique Antithrombin III binding domain of heparin.

Identification of a hexasaccharide sequence able to inhibit thrombin and suitable for 'polymerisation'

Three hexasaccharides, having from low to very high affinity for antithrombin, were synthesised from disaccharide building block precursors. One of them, methyl(sodium 2,3-di-O-methyl-4-O-sodium sulfonato-α-L-idopyranosyluronate)-(1→4)-[(2,3,6-tri-O-sodium sulfonato-α-D-glucopyranosyl)-(1→4)-(sodium 2,3-di-O-methyl-α-L-idopyranosyluronate)-(1→4)]2-2,3,6-tri-O-sodium sulfonato-α-D-glucopyranoside, obtainable from a single disaccharide building block precursor, constitutes a good starting point for obtaining simple oligosaccharidic heparin mimetics able to inhibit the two coagulation factors thrombin and Factor Xa. Copyright (C) 1999 Elsevier Science Ltd.