214468-42-5

Upstream product

• 83-87-4 D-glucose pentaacetate 
• 106-45-6 para-thiocresol 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 479252-05-6 ((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-p-tolylsulfanyl-tetrahydro-pyran-2-yl)-methanol 
• 762287-64-9 S-4-methylphenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside 
• 1582775-47-0 methyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranosyl-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside 
• 1582775-49-2 methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside 
• 1582775-53-8 methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside 
• 1582775-54-9 methyl β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside 
• 1582775-63-0 C₃₀H₄₂F₁₀N₂O₁₈ 
• 1582775-66-3 C₃₆H₅₀F₁₀N₂O₂₄ 
• 1582775-68-5 C₄₄H₆₀F₁₃N₃O₂₉ 

Relevant academic research and scientific papers

An Efficient Modular One-Pot Synthesis of Heparin-Based Anticoagulant Idraparinux

Idraparinux is a fully O-sulfated α-methyl glycoside of heparin pentasaccharide motif known to interact with the antithrombin III domain and act as anticoagulant. The current most effective synthesis of Idraparinux is complicated and nonstereoselective, requiring numerous stepwise procedures with low yields. We report here an efficient modular one-pot synthesis of Idraparinux involving the use of a glycosyl phosphate with 6-O-tert-butyl diphenyl silyl group and a d-glucuronic acid-containing disaccharide thioglycoside with 6-O-acetyl group as donor building blocks for the α-directing one-pot glycosylations with an l-iduronic acid-containing disaccharide acceptor building block. The uronic acid was incorporated in a disaccharide module used in the one-pot synthesis to avoid the complicated late-stage installation of these acidic sugars. The one-pot synthesis of Idraparinux demonstrated here is an effective strategy and should be applicable to the modular assembly of other heparan sulfates with regiodefined sulfation pattern for functional study.

NOVEL NEISSERIA MENINGITIDIS SEROGROUP Y OLIGOMER AND PROCESS FOR SYNTHESIZING THEREOF

The present invention relates to novel oligomers of Neisseria meningitidis serogroup Y capsular polysaccharide repeating unit (Men-Y oligomers) and process for synthesizing novel Men- Y oligomers. In particular, the present invention relates to the chemic

Fluorous-assisted chemoenzymatic synthesis of heparan sulfate oligosaccharides

The chemoenzymatic synthesis of heparan sulfate tetrasaccharide (1) and hexasaccharide (2) with a fluorous tag attached at the reducing end is reported. The fluorous tert-butyl dicarbonate (FBoc) tag did not interfere with enzymatic recognition

Epimeric and amino disaccharide analogs as probes of an α-(1→6)mannosyltransferase involved in mycobacterial lipoarabinomannan biosynthesist

Mycobacterial lipoarabinomannan (LAM) is an important, immunologically active glycan found in the cell wall of mycobacteria, including the human pathogen Mycobacterium tuberculosis. At the core of LAM is a mannan domain comprised of α-(1→6)-linked-mannopyranose (Manp) residues. Previously, we and others have demonstrated that α-Manp-(1→6)- α-Manp disaccharides (e.g., Manp-(1→6)-α-ManpOctyl, 1) are the minimum acceptor substrates for enzymes involved in the assembly of the LAM mannan core. We report here the synthesis five epimeric and three amino analogs of 1, and their subsequent biochemical evaluation against an α-(1→6)-ManT activity present in a membrane preparation from M. smegmatis. Changing the manno- configuration of either residue of 1 to talo- or gluco- led to a reduction or loss of activity, thus confirming earlier work showing that the C-2 and C-4 hydroxyl groups of each monosaccharide were important for enzymatic recognition. Characterization of the products formed from these analogs was done using a combination of mass spectrometry and glycosidase digestion, and full substrate kinetics were also performed. The analogs in which the acceptor hydroxyl group had been replaced with an amino group were, as expected, not substrates for the enzyme, but were weak inhibitors. The Royal Society of Chemistry 2010.

Concise synthesis of two trisaccharides related to the saponin isolated from Centratherum anthelminticum

Chemical synthesis of two trisaccharides related to the saponin isolated from Centratherum anthelminticum is reported. Stereoselective, high-yielding glycosylation strategies were developed using H2SO4 immobilized on silica for activ

Iterative one-pot synthesis of oligosaccharides

Straight to the point! Preactivation of a p-tolyl thioglycoside donor, followed by sequential addition of p-tolyl thioglycosyl acceptors in one reaction flask allowed rapid syntheses of oligosaccharides independent of anomeric reactivities of donors and a

pH dependent thermal stabilization of DNA by Glcβ(1→3) GlcNAcβ1-→STol

A disaccharide, Glcβ(1→3)GlcNAcβ1→STol (GGS, 1), was synthesized and demonstrated to stabilize ct-DNA during the denaturing process. GGS at 50 μM shifted Tm of ct-DNA by 23 °C and the behavior was pH dependent. Poly(dA-dT)2 was found

Use of acid-labile protective groups for carbohydrate moieties in synthesis of glycopeptides related to type II collagen

β-D-Galactopyranosyl and α-D-glucopyranosyl-β-D-galactopyranosyl moieties carrying silyl, isopropylidene and 4-methoxybenzyl protective groups have been attached to the amino acid 5-hydroxy-L-norvaline. The resulting glycosylated building blocks were used in Fmoc solid-phase synthesis of glycopeptides related to a fragment from type II collagen which is immunodominant in a mouse model for rheumatoid arthritis. The protective groups used for the carbohydrate moieties were completely removed during acid catalyzed cleavage of the glycopeptides from the solid phase under conditions which left the O-glycosidic bonds intact.