321380-28-3

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 74-88-4 methyl iodide 
• 1178888-20-4 C₁₅H₂₀O₇ 
• 98-88-4 benzoyl chloride 
• 175978-71-9 1,2,4,6-tetra-O-benzoyl-3-O-benzyl-β-L-idopyranose 
• 321380-20-5 methyl 2-O-benzoyl-3-O-benzyl-4,6-di-O-tert-butyldimethylsilyl-α-L-idopyranoside 
• 321380-62-5 (2R,3S,4R,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid 
• 321380-16-9 methyl 2-O-benzoyl-3-O-benzyl-4,6-O-isopropylidene-α-L-iodopyranoside 
• 181228-43-3 methyl 3-O-benzyl-4,6-O-isopropylidene-α-L-idopyranoside 
• 181024-52-2 methyl 2,4,6-tri-O-benzoyl-3-O-benzyl-α-L-idopyranoside 
• 181228-42-2 methyl 3-O-benzyl-α-L-idopyranoside 
• 321380-24-9 methyl (methyl 2-O-benzoyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosid)uronate 

Downstream Products

• 321380-47-6 methyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate 
• 321380-67-0 (2R,3S,4R,5R,6R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid 
• 321380-51-2 methyl (2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate 
• 1178888-27-1 C₅₀H₅₃N₃O₁₃ 
• 1258005-79-6 methyl 3-O-benzyl-α-L-idopyranoside uronic acid 
• 1416152-71-0 methyl (methyl (2-azido-3,6-di-O-benzyl-2-deoxy-4-O-trichloroacetyl-α-D-glucopyranosyl)-(1?4)-2-O-benzoyl-3-O-benzyl-α-L-idopyranoside) uronate 
• 445397-71-7 methyl O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->3)-(6-O-benzyl-2-deoxy-4-O-pivaloyl-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate 

Relevant academic research and scientific papers

Synthesis and mass spectrometric analysis of disaccharides from methanolysis of heparan sulfate

The quantification of heparan sulfate (HS) in biological matrices, e.g., urine, cerebrospinal fluid, tissue samples etc., is of great importance for the diagnosis and prognosis of several of the mucopolysaccharidosis (MPS) disorders, which are lysosomal storage diseases of impaired glycosaminoglycan metabolism. The development of suitable assays for this purpose is challenging due to the high molecular weight and complexity of HS. Recent efforts towards this goal include the acid catalysed methanolysis of HS, which desulfates the polymer and results in the formation of disaccharide cleavage products which can be detected and quantified by LC-MS/MS. We have synthesized a library of 12 HS-derived disaccharides as methanolysis standards via the stereoselective 1,2-cis glycosylation of suitably protected GlcA and IdoA acceptors with a 2-deoxy-2-azido thioglucoside donor. This facilitated identification of the major peaks in the LC-MS/MS chromatograms, and potentially will allow the monitoring of specific metabolites as surrogate markers for genotype. This work also paves the way towards a fully quantitative LC-MS/MS assay for HS via the preparation of a suitably labelled derivative.

Efficient chemical synthesis of heparin-like octa-, deca- and dodecasaccharides and inhibition of FGF2- and VEGF165-mediated endothelial cell functions

A concise chemical synthesis of a series of structurally-defined heparin-like oligosaccharides is described. This work provides an efficient entry to octa-, deca-, and dodecasaccharides, including the first synthesis of (GlcNS6S-IdoA2S)5 and (GlcNS6S-IdoA2S)6. Evaluation of the in vitro activity of these species against FGF2- and VEGF165- dependent endothelial cell proliferation and migration establishes that octa- and decasaccharides are more potent in targeting FGF2-induced effects, where cell migration is affected more significantly than proliferation. These structure-activity relationships exemplify the significance of 6-O-sulfation in regulating the activity of angiogenic growth factors.

Production Of L-Iduronate Containing Polysaccharides

A process for the production of polysaccharide (20) from disaccharide (10) and saccharide (21), wherein R1 to R10 are each independently the same or different protecting groups; R is an optionally substituted aryl group or an optiona

Syntheses of β-D-GalpNAc4SO3-(1→4)-L-IdopA2SO3, a disaccharide fragment of dermatan sulfate, and of its methyl α-L-glycoside derivative

The syntheses of sodium (sodium 2-acetamido-2-deoxy-4-O-sulfonato-β-D-galactopyranosyl)-(1→4)-(sodium 2-O-sulfonato-L-idopyran)uronate, a disaccharide fragment of dermatan sulfate, and of its methyl α-L-glycoside derivative are reported for the first time. The use of 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-1-O-trichloroaceti midoyl-α-D-galactopyranose, readily prepared from a D-gluco precursor, allowed the stereocontrolled and high yielding coupling with the low reactive 4-hydroxyl group of L-iduronic acid ester derivatives. Classical transformation of the disaccharide products into the target molecules was achieved in high yield. (C) 2000 Elsevier Science Ltd.