27894-87-7

Upstream product

• 28022-14-2 phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside 
• 2956-16-3 uridine 5'-diphospho-D-galactose 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide 
• 108-98-5 thiophenol 
• 5160-10-1 2,3,6-tetra-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-D-glucopyranosylbromide 
• 3616-19-1 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 
• 5328-50-7 D-cellobiose octaacetate 
• 5346-90-7 α-D-cellobiose octaacetate 
• 13360-52-6 Cellobiose 
• 20764-63-0 β-cellobioseoctaacetate 
• 14227-66-8 acetobromocellobiose 
• 69308-57-2 Acetic acid (3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 

Downstream Products

• 1032959-15-1 1-thiophenyl-4-O-(4',6'-O-benzylidiene-β-D-glucopyranosyl)-β-D-glucopyranoside 
• 88567-59-3 phenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 87470-77-7 phenyl 2,3,6,2',3',4'-hexa-O-benzyl-1-thio-β-cellobioside 
• 87470-78-8 phenyl 2,3,6,2',3',4'-hexa-O-benzyl-6'-O-methyl-1-thio-β-cellobioside 
• 87470-76-6 phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 895576-72-4 phenyl 4,6-O-benzylidene-β-D-glucopyranosyl-[1-4]-1-thio-β-glucopyranoside 
• 1345978-72-4 1-thiophenyl-2,3-diacetyl-6-O-tosyl-4-O-(2',3'-di-O-acetyl-4',6'-O-benzylidiene-β-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside 
• 1345978-74-6 1-thiophenyl-3,6-anhydro-4-O-(4',6'-O-benzylidiene-β-D-glucopyranosyl)-β-D-glucopyranoside 
• 1345978-76-8 1-thiophenyl-2-O-acetyl-3,6-anhydro-4-O-(2',3'-di-O-acetyl-4',6'-O-benzylidiene-β-D-glucopyranosyl)-β-D-glucopyranoside 
• 1345978-78-0 1-phenylsulfoxide-2-acetyl-3,6-anhydro-4-O-(2',3'-di-O-acetyl-4',6'-O-benzylidine-β-D-glucopyranosyl)-β-D-glucopyranoside 
• 1345978-80-4 C₂₇H₃₀Cl₃NO₁₃ 
• 1345978-70-2 1-thiophenyl-6-O-tosyl-4-O-(4',6'-O-benzylidiene-β-D-glucopyranosyl)-β-D-glucopyranoside 

Relevant academic research and scientific papers

Self-Promoted Glycosylation for the Synthesis of β-N-Glycosyl Sulfonyl Amides

N-Glycosyl N-sulfonyl amides have been synthesized by a self-promoted glycosylation, i. e. without any catalysts, promotors or additives. When the reactions were carried out at lower temperatures a mixture of N- and O-glycosides were observed, where the latter rearranged to give the β-N-glycosides at elevated temperatures. By this method sulfonylated asparagine derivatives can be selectively β-glycosylated in high yields by trichloroacetimidate glycosyl donors of different reactivity including protected glucosamine derivatives. The chemoselectivity in the glycosylations as well as the rearrangements from O-glycosides to β-N-glycosides gives information of the glycosylation mechanism. This method gives access to glycosyl sulfonyl amides under mild conditions.

Synthesis of Glycosylated 1-Deoxynojirimycins Starting from Natural and Synthetic Disaccharides

Iminosugars are an important class of natural products and have been subject to extensive studies in organic synthesis, bioorganic chemistry and medicinal chemistry, yet only a limited number of these studies are on glycosylated iminosugars. Here, a general route of synthesis is presented towards glycosylated 1-deoxynojirimycin derivatives based on the oxidation–reductive amination protocol that in the past has also been shown to be a versatile route towards 1-deoxynojirimycin. The strategy can be applied on commercial disaccharides, as shown in four examples, as well as on disaccharides that are not commercially available and are synthesized for this purpose, as shown by a fifth example.

Iridium catalysis: Reductive conversion of glucan to xylan

By using iridium catalysed dehydrogenative decarbonylation, we converted a partly protected cellobioside into a fully protected xylobioside. We demonstrate good yields with two different aromatic ester protecting groups. The resulting xylobioside was directly used as glycosyl donor in further synthesis of a xylooctaose.

Syntheses of cellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulases

Cellotriose and cellotetraose analogues carrying cyclohexene rings were developed as molecular probes which are expected to mimic the transition state conformation of hydrolysis by cellulases. The cyclohexene ring was placed at the pyranose ring being expected to locate the -1 subsite of the enzyme. In order to evaluate these probes, sulfur derivatives of cellotriose and cellotetraose were also synthesized as the enzyme tolerant analogues which mimic the stable conformations of the natural cellulose. The binding assays using differential scanning calorimetry revealed that introduction of the cyclohexene ring is effective to the complexation with an endoglucanase, NCE5 from Humicola insolens.

A study of anhydrocelluloses - Is a cellulose structure with residues in a 1C4-conformation more prone to hydrolysis?

A study of the effect of introduction of 3,6-anhydroglucose residues in the cellulose structure on glycoside hydrolysis rate was performed. A cellotetrose with an 3,6-anhydroglucose as the third residue was synthesised. Acidic hydrolysis of this tetrasacc

CELLOOLIGOSACCHARIDE DERIVATIVE AND PROCESS FOR PRODUCING THE SAME

A novel nonionic surfactant consisting of a cellooligosaccharide derivative wherein the position of introduction of hydrophobic groups is unevenly distributed along the main chain of cellulose; and a process for producing the same. There is provided a cellooligosaccharide derivative comprising a hydrophobic moiety of alkylated glucose or cellooligosaccharide and, bonded thereto in a block fashion, a hydrophilic moiety of monosaccharide or oligosaccharide.

An efficient glycosylation reaction for the synthesis of asialo GM2 analogues

We investigated the coupling reaction of glycosyl donors N-trichloroethoxycarbonyl-galactosamine-O-trichloroacetimidate (2a) and N-p-nitrobenzyloxycarbonyl-galactosamine-O-trichloroacetimidate (2b) with the 4′-OH of lactose derivatives (3a-d) to synthesiz

A facile protocol for direct conversion of unprotected sugars into phenyl 4,6-O-benzylidene-per-O-acetylated-1,2-trans-thioglycosides

A short and practical methodology for conversion of unprotected D-glucose, maltose, cellobiose and lactose into the corresponding phenyl 4,6-O-benzylidine-per-O-acetylated-1,2-trans-thioglycosides is described. The protocol is based on the execution of five reaction steps (bromoacetylation, thiophenolysis under phase transfer catalysis conditions, deacetylation, benzylidenation and acetylation) in one continuous procedure and provides a fast access to the title compounds as pure crystalline products without chromatographic purification.

Synthesis of a di- and a trisaccharide related to the antigen from Klebsiella type 16

Using methyl triflate as promoter, methyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1 → 4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate) and methyl O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1 → 4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl

Synthesis of ganglioside G(M3) and G(M4) analogs having mimics of ceramide moieties and their binding activities with influenza virus A

Ganglioside G(M4) (1) and G(M3) (2) analogs, which contain mimics of the ceramide moieties of gangliosides, were synthesized. The syntheses of 1 and 2 feature stereoselective glycosylation of methyl (phenyl 5-acetamido-4,7,8,9- tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-galacto-2-nonulopyranosid)onate (10) as the sialosyl donor with suitably protected galactose and lactose acceptors catalyzed by N-bromosuccinimide (NBS), iodine, and tetrabutylammonium trifluoromethanesulfonate (TBAOTf) as the glycosyl promoter in acetonitrile under kinetically controlled conditions. Compound 2 exhibited binding activity towards influenza virus A.