192505-53-6

Upstream product

• 215094-09-0 1,6-anhydro-2-O-benzyl-4-O-(tetrahydropyran-2-yl)-β-D-glucopyranose 
• 20194-18-7 sodium phenyl-methanolate 
• 67313-50-2 1,6:2,3-dianhydro-4-O-(tetrahydropyran-2-yl)-β-D-mannopyranose 

Downstream Products

• 192505-55-8 C₄₆H₆₀Cl₃NO₁₉ 
• 192505-54-7 (2S,3S,4S,5R,6R)-6-((1R,2R,3S,4R,5R)-3-Acetoxy-4-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-3-((2R,3S,4R,5R,6R)-6-acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Introducing a C-interglycosidic bond in a biologically active pentasaccharide hardly affects its biological properties

We describe here the synthesis and the biological activity of a 'C-pentasaccharide', a new analogue of the antithrombin III (AT III) binding region of heparin containing a methylene bridge in place of an interglycosidic oxygen atom. The affinity for AT III and the anti-factor Xa activity of this compound have been compared with that of the corresponding selected 'O-pentasaccharide'. Such a structural modification slightly decreased the affinity of this compound for AT III as well as its anti-factor Xa activity (880±40 anti-Xa units versus 1180±30 anti-Xa units for the C-pentasaccharide and the O-pentasaccharide, respectively). This compound therefore represents the first example of a new class of anti-factor Xa pentasaccharides containing a C-interglycosidic bond. Copyright (C) 1998 Elsevier Science Ltd.

Synthesis and biological activity of a new anti-factor Xa pentasaccharide with a C-interglycosidic bond

A mixed synthetic C, O-pentasaccharide 17 has been synthesized and shown to display an anti-factor Xa activity similar to that of the corresponding O-pentasaccharide 18. 17 represents the first example of a synthetic C-oligosaccharidic mimetic eliciting a significant biological response.