507485-63-4

Upstream product

• 507485-62-3 methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-4-O-tetrahydropyranyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 507485-55-4 (2R,3S,4R,4aS,9aS)-2-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methoxy-6,6-dimethyl-9a-vinyl-hexahydro-1,5,7-trioxa-benzocyclohepten-3-ol 
• 507485-53-2 methyl 2,3,6-tri-O-benzyl-4-O-(4,7-O-isopropylidene-6-deoxy-3-O-methyl-5-C-vinyl-β-D-gluco-heptopyranosyl)-α-D-glucopyranoside 
• 507485-54-3 methyl 2,3,6-tri-O-benzyl-4-O-(2-O-acetyl-6-deoxy-3-O-methyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside 
• 507485-56-5 Acetic acid (2R,3S,4S,4aS,9aS)-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methoxy-6,6-dimethyl-9a-vinyl-hexahydro-1,5,7-trioxa-benzocyclohepten-3-yl ester 
• 507485-52-1 methyl 2,3,6-tri-O-benzyl-4-O-(2,4,7-tri-O-acetyl-6-deoxy-3-O-methyl-5-C-vinyl-β-D-gluco-heptopyranosyl)-α-D-glucopyranoside 
• 507485-59-8 methyl 2,3,6-tri-O-benzyl-4-O-(2-O-acetyl-6-deoxy-3-O-methyl-4-O-tetrahydropyranyl-7-O-tosyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside 
• 1054659-84-5 methyl 2,3,6-tri-O-benzyl-4-O-(2-O-acetyl-6-deoxy-3-O-methyl-7-O-tosyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside 

Downstream Products

• 507485-64-5 methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-5-C-benzyloxycarbonyl-3-O-methyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside 

Relevant academic research and scientific papers

Further evidence for the critical role of a non-chair conformation of L-iduronic acid in the activation of antithrombin

L-iduronic acid, a conformationally flexible monosaccharide, imparts a remarkable protein adaptability to the glycosaminoglycans heparin, heparan sulfate, and dermatan sulfate. The pentasaccharide representing the antithrombin binding site of heparin contains one such L-iduronic acid residue, the conformation of which has been suspected for a long time to be a critical factor in the interaction with antithrombin. We have recently synthesized pentasaccharides containing an L-iduronic acid residue conformationally forced to exist within a restricted arc (2S0 ? 2,5B ? 5S1) of the overall pseudorotational circle. We could thus demonstrate that the 2S0 conformation is adopted upon binding to the protein. In the present work, we now describe the synthesis of a similar pentasaccharide containing a slightly more flexible L-iduronic acid unit with a three-atom bridge between C-2 and C5 of the hexopyranose ring. This pentasaccharide is a better activator of AT-III with respect to blood coagulation factor Xa inhibition. These results confirm that L-iduronic acid adopts an unusual non-chair conformation close to 2S0 and clearly explains how the unique conformational behavior of L-iduronic acid is the key to heparin's interaction with AT-III. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.