29388-46-3

Upstream product

• 13035-24-0 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 64-19-7 acetic acid 
• 149831-94-7 methyl 2,3-di-O-benzyl-4,6-di-O-isopropylidene-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 709-50-2 methyl beta-D-glucopyranoside 
• 101312-02-1 methyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside 
• 71117-37-8 (2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 100-44-7 benzyl chloride 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 
• 122079-59-8 methyl 2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranoside 
• 71117-36-7 methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 
• 162426-14-4 methyl 4,6-O-benzylidene-β-D-galactopyranoside 2,3-di-O-benzoate 
• 78103-35-2 (4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-methoxy-2-(4-methoxy-phenyl)-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 4288-93-1 methyl 4,6-O-benzylidene-α-D-galactopyranoside 

Downstream Products

• 51842-38-7 methyl 2,3-di-O-benzyl-6-O-trityl-β-D-glucopyranoside 
• 148312-82-7 methyl (methyl-2,3-bis-O-(phenylmethyl)-β-D-glucopyranoside)uronate 
• 112260-58-9 methyl 2,3-di-O-benzyl-4,6-bis-O-(trifluoromethanesulfonyl)-β-D-glucopyranoside 
• 124040-33-1 methyl 2,3-di-O-benzyl-β-D-glucopyranoside 4,6-di-(phenylsulfate) 
• 124040-31-9 methyl 2,3-di-O-benzyl-β-D-glucopyranoside 6-(phenylsulfate) 
• 20771-16-8 Methyl 4,6-di-O-acetyl-2,3-di-O-benzyl-β-D-glucopyranoside 
• 161518-50-9 Methyl 4-O-acetyl-2,3-di-O-benzyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 161518-54-3 Methyl 2,3-di-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 4356-80-3 methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 19488-61-0 methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside 
• 19488-49-4 methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 79698-16-1 methyl 4,6-di-O-benzoyl-2,3-di-O-benzyl-β-D-glucopyranoside 
• 31873-35-5 methyl 6-O-benzoyl-2,3-di-O-benzyl-β-D-glucopyranoside 
• 74801-22-2 methyl 2,3-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-4-O-(methylsulfonyl)-β-D-glucopyranoside 

Relevant academic research and scientific papers

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.

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.

A green and convenient method for regioselective mono and multiple benzoylation of diols and polyols

An efficient method for regioselective benzoylation of diols and polyols was developed. The benzoylation is catalyzed by only 0.2 equiv of benzoate anion in acetonitrile with the addition of a stoichiometric amount of benzoic anhydride under very mild condition, leading to high yields. Compared with all other methods, this method shows particular advantage in regioselective multiple benzoylation of polyols, and in avoiding the use of any metal-based catalysts and any amine bases, which is more environment-friendly.

Regioselective mono and multiple alkylation of diols and polyols catalyzed by organotin and its applications on the synthesis of value-added carbohydrate intermediates

A catalytic amount of dibutyltin dichloride was used to develop regioselective alkylation of diols and multiple alkylation of polyols. Alkyl groups, including allyl, alkynyl and long-chain alkyl groups, were successfully introduced to one or two hydroxyl

Selective 4,6-O-benzylidene formation of methyl α-d-mannopyranoside using 2,6-dimethylbenzaldehyde

While methyl α-d-glucopyranosides and α-d-galactopyranosides selectively form 4,6-O-benzylidenes when reacted with excess benzaldehyde in the presence of acid catalyst methyl α-d-mannopyranosides does not exhibit the same selectivity because of the cis-ar

Enantioselective alkylation of aldehydes using dialkylzincs catalyzed by simple chiral diols derived from naturally occurring monosaccharides

Enantioselective alkylation of aldehydes was achieved in up to 84% ee using dialkylzincs catalyzed by simple diols derived from naturally occurring monosaccharides.

Synthesis of oligosaccharide fragments of the rhamnogalacturonan of Nerium indicum

Three trisaccharides, one pentasaccharide, and one heptasaccharide, namely α-D-GalA-(1→2)-α-L-Rha-(1→4)-β-D-GalA-OC 3H7 (1), α-L-Rha-(1→4)-α-D-GalA- (1→4)-β-D-GalA-OC3H7 (2), α-D-GalA- (1→4)-α-DGalA-(1→2)-α-L-Rh

Halide promoted organotin-mediated carbohydrate benzylation: Mechanism and application

In the present study, the mechanistic origin of the promoted organotin-mediated carbohydrate benzylation by halides was explored by the comparison of the activation ability of halides on benzylation of methyl β-d-galactoside. It was demonstrated that the

Cleavage of 4,6- O -benzylidene acetal using sodium hydrogen sulfate monohydrate

The use of protecting groups is an important protocol in carbohydrate synthesis. Among protecting groups, benzylidene acetals are generally more stable than other acetals; therefore, strong conditions are often required for deprotection. We report the deprotection of 4,6-O-benzylidene derivatives using sodium hydrogen sulfate monohydrate under mild conditions. Georg Thieme Verlag Stuttgart New York.

Construction of triazolyl bidentate glycoligands (TBGs) by grafting of 3-azidocoumarin to epimeric pyranoglycosides via a fluorogenic dual click reaction

Glycoligands, which feature a glycoside as the central template incorporating Lewis bases as metal chelation sites and various fluorophores as the chemical reporter, represent a range of interesting scaffolds for development of chemosensors. Here, new typ