148312-82-7

Upstream product

• 186581-53-3 diazomethane 
• 6988-40-5 methyl 2,3-di-O-benzyl-β-D-glucopyranoside 
• 101312-02-1 methyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside 
• 74-88-4 methyl iodide 
• 709-50-2 methyl beta-D-glucopyranoside 
• 117605-33-1 methyl 4,6-O-(4’-methoxybenzylidene)-α-D-glucopyranoside 
• 67-56-1 methanol 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 51433-18-2 O²,O³-dibenzyl-O¹,O⁴-dimethyl-α-D-glucopyranuronic acid methyl ester 
• 161545-35-3 methyl 4)-2,3-di-O-benzyl-β-D-glucopyranosid>uronate 
• 31506-18-0 Methyl uronate 
• 51885-48-4 O¹,O⁴-dimethyl-α-D-glucopyranuronic acid amide 
• 112047-66-2 O²,O³-dibenzyl-O¹,O⁴-dimethyl-α-D-glucopyranuronic acid amide 

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.

Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity

The reactivity of both coupling partners—the glycosyl donor and acceptor—is decisive for the outcome of a glycosylation reaction, in terms of both yield and stereoselectivity. Where the reactivity of glycosyl donors is well understood and can be controlled through manipulation of the functional/protecting-group pattern, the reactivity of glycosyl acceptor alcohols is poorly understood. We here present an operationally simple system to gauge glycosyl acceptor reactivity, which employs two conformationally locked donors with stereoselectivity that critically depends on the reactivity of the nucleophile. A wide array of acceptors was screened and their structure–reactivity/stereoselectivity relationships established. By systematically varying the protecting groups, the reactivity of glycosyl acceptors can be adjusted to attain stereoselective cis-glucosylations.

Development of an azanoradamantane-type nitroxyl radical catalyst for class-selective oxidation of alcohols

The development of 1,5-dimethyl-9-azanoradamantane N-oxyl (DMN-AZADO; 1,5-dimethyl-Nor-AZADO, 2) as an efficient catalyst for the selective oxidation of primary alcohols in the presence of secondary alcohols is described. The compact and rigid structure of the azanoradamantane nucleus confers potent catalytic ability to DMN-AZADO (2). A variety of hindered primary alcohols such as neopentyl primary alcohols were efficiently oxidized by DMN-AZADO (2) to the corresponding aldehydes, whereas secondary alcohols remained intact. DMN-AZADO (2) also has high catalytic efficiency for one-pot oxidation from primary alcohols to the corresponding carboxylic acids in the presence of secondary alcohols and for oxidative lactonization from diols.

9-azanoradamantane N—oxyl compound and method for producing same, and organic oxidation catalyst and method for oxidizing alcohols using 9-azanoradamantane N—oxyl compound

An organocatalyst for oxidizing alcohols in which a primary alcohol is selectively oxidized in a polyol substrate having a plurality of alcohols under environmentally-friendly conditions. The organic oxidation catalyst has an oxygen atom bonded to a nitrogen atom of an azanoradamantane skeleton and at least one alkyl group at positions 1 and 5. The oxidation catalyst has higher activity than TEMPO, which is an existing oxidation catalyst, in the selective oxidation reaction of primary alcohols, and better selectivity than AZADO and 1-Me-AZADO. This DMN-AZADO can be applied to the selective oxidation reaction of primary alcohols that contributes to shortening the synthesizing process for pharmaceuticals, pharmaceutical raw materials, agricultural chemicals, cosmetics, organic materials, and other such high value-added organic compounds.

Selective oxidation of monosaccharide derivatives to uronic acids

Primary hydroxyl groups in partially protected monosaccharide derivatives were selectively oxidised to carboxylic acids using sodium hypochlorite in the presence of catalytic amounts of 2,2,6,6-tetramethyl-1-piperidinyl oxy, free radical (TEMPO). Acetal,