150809-76-0

Upstream product

• 1666-13-3 diphenyl diselenide 
• 4098-06-0 triacetyl-D-galactal 

Downstream Products

• 862851-12-5 phenyl 2-azido-2-deoxy-1-seleno-α-D-galactopyranoside 
• 317816-84-5 Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-tert-butoxycarbonylamino-6-phenylselanyl-tetrahydro-pyran-4-yl ester 
• 317816-83-4 Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-phenylselanyl-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-4-yl ester 
• 161822-74-8 Phenyl 2-(N-acetylamino)-3,4,6-tri-O-acetyl-2-deoxy-1-seleno-α-D-galactopyranoside 
• 100929-00-8 benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate 
• 100938-55-4 N-(9H-fluorene-9-yl)-methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester 
• 197795-16-7 3-trifluoroacetamidopropyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside 
• 100496-17-1 3-trifluoroacetamidopropyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranoside 

Relevant academic research and scientific papers

Azido-phenylselenylation of protected glycals

Anti-Markovnikov azido-phenylselenylation of diversely protected glycals affords protected phenyl 2-azido-2-deoxy-α-selenoglycopyranosides. From D-glucal, the α-manno and α-gluco isomers are obtained, whereas from D-galactal, a complete stereocontrol is observed, affording exclusively the α-galacto isomer in 70% yield.

Chemical synthesis of the Pseudomonas aeruginosa O11 O-antigen trisaccharide based on neighboring electron-donating effect

Pseudomonas aeruginosa O11 O-antigen is immunologically active but an exact protective epitope has not yet been identified. Synthesis of O11 O-antigen trisaccharide is of importance for identifying the epitopes. Here, neighboring electron-donating effects are keys to enhance the nucleophilicity of the C3 hydroxyl groups of D- and L-fucosamines, to facilitate the efficient synthesis of the trisaccharide. The disarmed peracetylated glycosyl donor with low glycosylation reactivity and glycosyl trifluoroacetimidate with good stability allowed for the glycosylation under mild conditions. The C6 nucleophilic tosylate substitution of D-galactose with iodine was found to be dependent on the steric effect of the axial C4.

Biotinylated Oligo-α-(1 → 4)-d-galactosamines and Their N-Acetylated Derivatives: α-Stereoselective Synthesis and Immunology Application

Using 3-O-benzoyl-4,6-O-di-tert-butylsilylidene-2-azido-2-deoxy-selenogalactoside, biotinylated oligo-α-(1 → 4)-d-galactosamines comprising from two to six GalN units were prepared for the first time together with their N-acetylated derivatives. The combination of blocking groups used herein provided stereocontrol for the α-stereospecific glycosylation, to show also high efficiency of phenyl 2-azido-2-deoxy-selenogalactosides as glycosyl donors. The obtained glycoconjugates are related to fragments of exopolysaccharide galactosaminogalactan (GG) found in Aspergillus fumigatus, which is the most important airborne human fungal pathogen in industrialized countries. The synthesized glycoconjugates were arrayed on streptavidin-coated plates and used to investigate the GG epitopes recognized by mouse monoclonal antibodies against GG and by human antibodies in the sera of patients with aspergillosis. The obtained data showed that the oligo-α-(1 → 4)-d-galactosamines and their N-acetylated derivatives allowed the first precise analysis of the specificity of the antibody responses to this extremely complex fungal polysaccharide.

Homogeneous azidophenylselenylation of glycals using TMSN 3-Ph2Se2-PhI(OAc)2

The use of TMSN3 instead of NaN3 allows the reaction to be performed under homogeneous conditions, shortens the reaction time, and provides reliable scale-up. An improved preparative method for homogeneous azidophenylselenylation of glycals is described consisting of reaction with TMSN3 and Ph2Se2 in the presence of PhI(OAc)2. The use of TMSN3 instead of NaN3 as in the heterogeneous procedure, allowed both a reduced reaction time and a scale-up that was not possible in the case of the azidophenylselenylation of substituted glycals using NaN3.

Safe and Scalable Continuous Flow Azidophenylselenylation of Galactal to Prepare Galactosamine Building Blocks

Differentially protected galactosamine building blocks are key components for the synthesis of human and bacterial oligosaccharides. The azidophenylselenylation of 3,4,6-tri-O-acetyl-d-galactal provides straightforward access to the corresponding 2-nitrog

Further Investigation of the 2-Azido-phenylselenylation of Glycals

Derivatives of 2-azido-2-deoxysugars are widely applied as precursor of 2-amino-2-deoxysugars in the synthesis of various oligosaccharides of bacterial, fungal and mammalian origin. Heterogeneous or homogeneous azidophenylselenylation (APS) of glycals, i. e., reaction of glycals with Ph2Se2, PhI(OAc)2 and NaN3 or TMSN3 as azide radical donors, is a straightforward way to phenyl 2-azido-2-deoxy-1-selenoglycosides that can be directly used as glycosyl donors. However, heterogeneous APS is characterized by insufficient reproducibility and scalability. We have studied the effect of reaction conditions on the product distribution in heterogeneous APS of 3,4,6-tri-O-acetyl-d-galactal and found the conditions that enabled reliable preparation of crystalline phenyl 2-azido-2-deoxy-1-seleno-α-d-galactopyranoside triacetate in yield of 58 % on the 3.7 mmol scale. APS of 3,4,6-tri-O-acetyl-d-glucal under those conditions produced a ～1 : 1 mixture of phenyl 2-azido-2-deoxy-1-seleno-α-d-gluco- and mannopyranosides in total yield of 78 %. Acetoxyphenylselenylation of differently protected galactals and 3,4,6-tri-O-acetyl-d-glucal under the action of Ph2Se2 and PhI(OAc)2 has been shown to be a convenient method for the synthesis of 1-O-acetyl-2-seleno-2-deoxy derivatives, valuable intermediates in chemistry of 2-deoxysugars. 2-Seleno-2-deoxy sugars were characterized in detail by NMR data including 77Se chemical shifts and nJSe?H coupling constant values.

Chemical synthesis method of Bacillus pyocyaneus 011 serotype O antigen oligosaccharide

The invention discloses a chemical synthesis method of Bacillus pyocyaneus 011 serotype O antigen oligosaccharide, and belongs to the field of chemistry. The method comprises the steps that a D-glucose block, an L-fucosamine block and a D-fucosimide block are utilized to construct O antigen trisaccharide, wherein the D-glucose block or the L-fucosamine block is connected with the D-fucosimide block through a 1,2-alpha-cis-glycosidic bond, the D-glucose block is connected with the L-fucososamine block through a 1,2-alpha-trans-glycosidic bond, and the 1,2-alpha-cis-glycosidic bond is constructed in a mixed solvent; the mixed solvent comprises two or more of dichloromethane, diethyl ether and thiophene. The method has the advantages that D-mannose is utilized as a raw material to obtain D-fucose simply, conveniently and efficiently; the uniform construction of the cis-glycosidic bond is achieved by relying on the appropriate mixed solvent; the stereoselectivity can reach 100%; and the method has a good application prospect in the development of novel drugs and vaccines for resisting Bacillus pyocyaneus and the like.

A study of the mechanism of the azidophenylselenylation of glycals

Chemical and physicochemical studies of homogeneous azidophenylselenylation of glycols with diacetoxyiodobenzene, trimethylsilyl azide, and diphenyl diselenide in dichloromethane revealed that the most probable key reaction step is the formation of phenylselenyl azide, an azide radical donor. A method for azidophenylsulfenylation of glycals was proposed.

Radical-mediated synthesis of α-C-glycosides based on N-acyl galactosamine

(Matrix presented) C-glycoside analogue of O-benzyl α-D-GalNAc C-Glycosides of N-acyl 2-amino-2-deoxygalactose (acyl = MeCO, CF3CO, t-BuOCO) are available in a stereoselective manner by trapping of an anomeric radical with an activated alkene.

A concise synthesis of the O-glycosylated amino acid building block; using phenyl selenoglycoside as a glycosyl donor

A new glycosylation methodology for synthesizing a protected TF antigen is described. The key step is to use phenyl selenoglycoside as a glycosyl donor, thereby successfully establishing O-linked Fmoc-protected threoninyl monosaccharide in an excellent yi