323195-40-0

Upstream product

• 98-88-4 benzoyl chloride 
• 219518-19-1 4-methylphenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 106-45-6 para-thiocresol 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 755002-56-3 p-tolyl 2-O-benzoyl-4,6-O-(R)-benzylidene-1-thio-β-D-glucopyranoside 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 
• 83-87-4 D-glucose pentaacetate 

Downstream Products

• 1259930-24-9 p-tolyl 2,3-di-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside 
• 1333393-38-6 p-tolyl 4,6-O-benzylidene-2,3-di-O-benzyl-D-galactopyranosyl-α(1→6)-2,3-di-O-benzoyl-4-O-benzyl-thio-β-D-glucopyranoside 
• 1352561-84-2 C₅₁H₅₆O₁₃ 
• 1352561-87-5 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 1419180-54-3 p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→4)-2-O-benzyl-3-O-(4-methoxybenzyl)-β-L-fucopyranoside 
• 1407151-58-9 p-tolyl 6-O-acetyl-2,3-di-O-benzoyl-4-O-benzylthio-β-D-glucopyranoside 
• 1616968-84-3 p-methoxyphenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzyl-β-L-fucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-benzyl-β-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside 
• 1262589-19-4 p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside 
• 1111726-67-0 propargyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4-O-(2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside 
• 323195-43-3 p-methylphenyl 2,3-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis and Immunological Studies of Oligosaccharides that Consist of the Repeating Unit of Streptococcus pneumoniae Serotype 3 Capsular Polysaccharide

A highly convergent and efficient strategy was developed for the chemical synthesis of complex oligosaccharides of Streptococcus pneumoniae type 3 capsular polysaccharides that contain multiple glucuronic acid units. Once the oligoglucosides were efficiently and stereoselectively assembled, the designated glucose units were regioselectively oxidized to glucuronic acid in one step at the final synthetic stage, which helped avoid difficult glycosylations that involved glucuronic acid. The target oligosaccharides had a free amino group at the reducing terminus and varied caps at the non-reducing terminus to enable further modification and structure–activity relationship studies. Immunological evaluations of the oligosaccharide–tetanus toxoid conjugates showed that they elicited robust T-cell-dependent immunoglobulin G antibody responses and that the sugar chain length had a major impact on their immunological properties. In particular, the penta- and hexasaccharides were identified as promising antigens for vaccine development.

Convergent Synthesis of Branched β-Glucan Tridecasaccharides Ready for Conjugation

Structurally defined and pure oligosaccharides corresponding to β-glucans have attracted great attention because of their potential properties as immunostimulating agents and as antigens of vaccine candidates. We herein describe a convergent synthesis of ready-to-conjugate tridecasaccharides composed of a β-1,3-glucan nonasaccharide backbone and a β-1,6-glucan tetrasaccharide branch. The assembly was achieved by employing trichloroacetimidate glycosylations and features the gram-scale preparation of the nonasaccharide backbone and installation of the tetrasaccharide branch involving orthoester rearrangement to the glycoside.

Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions

The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.

Key disaccharide repeat unit of glucuronic mannan oligosaccharide and preparation method of key disaccharide repeat unit

The invention provides a skeleton structure of a key disaccharide repeat unit of glucuronic mannan oligosaccharide and a preparation method of the skeleton structure. According to the key disacchariderepeat unit, glucose and mannose are used as raw materials, the key disaccharide repeat unit of glucuronic mannan oligosaccharide for treating or/and preventing Parkinson's disease and nephropathy isprepared through simple and easy-to-implement synthesis steps, and leaving groups of the key disaccharide repeat unit can be used as a glycosyl donor after being modified. The glucuronic acid can beused as a glycosyl receptor after four-position hydroxyl protecting groups of the glucuronic acid are removed, can be conveniently used for extending a carbohydrate chain of glucuronic mannan oligosaccharide, and has a key application value in the field of synthesis of the glucuronic mannan oligosaccharide.

Oligosaccharide conjugate based on Streptococcus pneumoniae type 3 capsular polysaccharide, preparation method and applications thereof

The present invention relates to an oligosaccharide conjugate based on Streptococcus pneumoniae type 3 capsular polysaccharide, a preparation method and applications thereof, wherein the structure general formula of the oligosaccharide conjugate is define

Unusually Stable Picoloyl-Protected Trimethylsilyl Glycosides for Nonsymmetrical 1,1′-Glycosylation and Synthesis of 1,1′-Disaccharides with Diverse Configurations

Nonsymmetrical 1,1′-disaccharides and related derivatives constitute structural components in various glycolipids and natural products. Some of these compounds have been shown to exhibit appealing biological properties. We report a direct yet stereoselective 1,1′-glycosylation strategy for the synthesis of nonsymmetrical 1,1′-disaccharides with diverse configurations and sugar components. The strategy is based on the joined forces of a new class of configurationally stable glycoside acceptors and stereodirecting thioglycoside donors. The new glycoside acceptors feature a picoloyl (Pico) protecting group at the remote C4/C3 position that confers unusual stability on TMS glycosides under acidic conditions.

A convergent synthesis of 6-o-branched β-Glucan oligosaccharides

β-Glucans are important carbohydrate antigens that are found on the surface of fungal cells, and they could be useful for the development of antifungal vaccines. This paper describes a highly convergent and efficient strategy for the synthesis of structur

Solvent participation in a one-pot glycosylation strategy (SPOG)

Solvent participation in a one-pot glycosylation strategy (SPOG) was developed on the basis of the low concentration β-selective glycosylation method. This strategy enables the production of a β-glycosidic bond in a one-pot oligosaccharide synthesis without or with minimal use of any C-2 participating function.

Ultrasonication-assisted spray ionization mass spectrometry for on-line monitoring of organic reactions

A straightforward on-line monitoring of organic reactions by ultrasonication-assisted spray ionization mass spectrometry (UASI MS) is demonstrated in this work.

Synthesis of oligosaccharides related to a biodynamic saponin from Calamus Insignis as their propargyl glycosides

The total synthesis of the carbohydrate portion (penta-and tetrasaccharides) of steroidal saponins, isolated from Calamus insignis, is reported. A simple route is followed, starting from commercially available D-glucose and L-rhamnose, through high-yielding protecting group manipulation strategies. Sulfuric acid immobilized on silica (H2SO 4/silica) was used as an effective Broensted acid source in conjunction with N-iodosuccinimide for activation of thioglycosides or alone for trichloroacetimidate donors in key glycosylation steps. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.