87326-76-9

Upstream product

• 87326-73-6 (S)-methyl 2-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyacetate 
• 116-11-0 2-Methoxypropene 
• 87326-77-0 methyl 3-O-benzyl-L-idopyranosyluronate 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 915154-71-1 3-O-benzyl-1,2-O-isopropylidene-β-L-idopyranuronamide 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 100-39-0 benzyl bromide 
• 67-56-1 methanol 
• 262382-45-6 tris(thiophenyl) 3-O-benzyl-1,2-O-isopropylidene-β-L-orthoidofuranuronate 
• 74-88-4 methyl iodide 
• 87326-75-8 (R)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester 
• 92955-34-5 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-6-O-trityl-α-D-glucofuranose 
• 37073-70-4 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-trityloxyethanol 

Downstream Products

• 93382-47-9 methyl (acetyl 2,4-di-O-acetyl-3-O-benzyl-α,β-L-idopyranoside)uronate 
• 87326-77-0 methyl 3-O-benzyl-α-L-idopyranuronate 
• 87326-78-1 methyl 3-O-benzyl-β-L-idopyranuronate 
• 87326-77-0 methyl 3-O-benzyl-L-idopyranosyluronate 
• 444118-44-9 1,2-O-isopropylidene-3-O-benzyl-4-O-trichloroacetyl-6-methyl-α-L-idonic acid 
• 615542-95-5 methyl 4-O-allyl-3-O-benzyl-1,2-O-isopropylidene-α-L-idopyranosiduronate 
• 615542-98-8 methyl 3,4-di-O-benzyl-1,2-O-isopropylidene-α-L-idopyranosiduronate 
• 615543-24-3 methyl 1,2-di-O-acetyl-4-O-allyl-3-O-benzyl-β-L-idopyranosiduronate 
• 615543-00-5 methyl 3-O-benzyl-1,2-O-isopropylidene-4-O-levulinoyl-α-L-idopyranosiduronate 
• 615543-04-9 methyl 2-O-acetyl-4-O-allyl-3-O-benzyl-L-idopyranosiduronate trichloroacetimidate 
• 615543-20-9 methyl 2-O-acetyl-3-O-benzyl-4-O-levulinoyl-L-idopyranosiduronate trichloroacetimidate 
• 615543-18-5 methyl 3-O-benzyl-4-O-levulinoyl-2-O-pivaloyl-L-idopyranosiduronate trichloroacetimidate 

Relevant academic research and scientific papers

Formal synthesis of a disaccharide repeating unit (IdoA-GlcN) of heparin and heparan sulfate

A concise route to access the key disaccharide repeating unit (IdoA-GlcN) of heparan sulfate is described. The synthesis was accomplished by commercially available diacetone α-d-glucose to functional group transformations, which led to the formation of a

PROCESS FOR PREPARING HEPARINOIDS AND INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF

Processes are disclosed for the synthesis of the Factor Xa anticoagulant fondaparinux and related compounds. Protected pentasaccharide intermediates and efficient and scalable processes for the industrial scale production of fondaparinux sodium by conversion of the protected pentasaccharide intermediates via a sequence of deprotection and sulfonation reactions are provided.

Toward the assembly of heparin and heparan sulfate oligosaccharide libraries: efficient synthesis of uronic acid and disaccharide building blocks

The monosaccharide moieties found in heparin (HP) and heparan sulfate (HS), glucosamine and two kinds of uronic acids, glucuronic and iduronic acids, were efficiently synthesized by use of glucosamine hydrochloride and glucurono-6,3-lactone as starting compounds. In the synthesis of the disaccharide building block, the key issues of preparation of uronic acids (glucuronic acid and iduronic acid moieties) were achieved in 12 steps and 15 steps, respectively, without cumbersome C-6 oxidation. The resulting monosaccharide moieties were utilized to the syntheses of HP/HS disaccharide building blocks possessing glucosamine-glucuronic acid (GlcN-GlcA) or iduronic acid (GlcN-IdoA) sequences. The disaccharide building blocks were also suitable for further modification such as glycosylation, selective deprotection, and sulfation.

Scalable synthesis of L-lduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides

L-ldo cyanohydrln 3 was prepared from dlacetone-D-glucose In four steps and 76% overall yield and 90% de via cyanohydrin reaction of aldehyde 2. This process can be scaled to provide >1 mol of pure L-Ido cyanohydrin 3. Cyanohydrin 3 was elaborated to 1,2-Isopropylldineprotected L-ldo nitrile (8), lduronic amide 9, and known carboxy ester 10. Coupling of 8 and 9 with glucosamine donors leads to new types (6-cyano and 6-carboxamlde) of heparin-related disaccharides.

Compounds that bind to the interferon-gamma, preparation method thereof and medicaments containing same

Compound capable of binding to gamma-interferon (γ-IFN), chosen from the molecules corresponding to formula (I) below: in which X is a divalent spacer group that is sufficiently long to allow the two oligosaccharide fragments A and B to each bind to one of the peptide sequences 125 to 143 of the C-terminal ends of a γ-interferon (γ-IFN) homodimer, n represents an integer from 0 to 10, and for example equal to 0, 1, 2, 3, 4 or 5, and each R independently represents a hydrogen atom, an SO3? group or a phosphate group, on the condition that no SO3? group is in the 3-position of the glucosamine units of compound (I). The invention also relates to the process for preparing these compounds, to the complexes formed by these compounds and gamma-interferon, and to the medicaments comprising these compounds or complexes.

Modular synthesis of heparin oligosaccharides

A general, modular strategy for the first completely stereoselective synthesis of defined heparin oligosaccharides is described. Six monosaccharide building blocks (four differentially protected glucosamines, one glucuronic and one iduronic acid) were uti

Efficient preparation of three building blocks for the synthesis of heparan sulfate fragments: Towards the combinatorial synthesis of oligosaccharides from hypervariable regions

New, multigram routes to suitably protected L-iduronyl monosaccharide donors 4 and 5 and 2-azidoglucose acceptors 6 and 7 are described. The L-iduronyl and D-glucuronyl disaccharides 1-3 were then prepared from these compounds, by means of efficient and regioselective protective group manipulations. These disaccharides form the basis of a combinatorial approach toward the synthesis of heparan sulfate fragments representative of the heterogeneous regions of this polysaccharide. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)Introduction.

Synthesis of iduronic acid building blocks for the modular assembly of glycosaminoglycans

The modular synthesis of glycosaminoglycans requires straightforward methods for the production of large quantities of protected uronic acid building blocks. In particular, the preparation of fully differentiated iduronic acids has proven particularly cha

Efficient selective preparation of methyl-1,2,4-tri-O-acetyl-3-O-benzyl-β-L-idopyranuronate from methyl 3-O-benzyl-L-iduronate

Methyl 1,2,4-tri-O-acetyl-3-O-benzyl-L-idopyranuronate 6β/6α, prepared from methyl 3-O-benzyl-L-iduronate (4), is a key synthon in heparin/heparan sulfate synthesis. The 1H and 13C NMR spectra of the furanose-pyranose mixture of 4, a

Conformational locking of the glycosyl acceptor for stereocontrol in the key step in the synthesis of heparin

Complete control over the stereoselectivity of key coupling reactions in the synthesis of heparin can be exerted by conformationally locking the uronic acid acceptor (see scheme).