6619-07-4

Basic information

• Product Name: Toluene-4-sulfonic acid (2S,3S,4S,5S)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester
• CAS NO: 6619-07-4
• Molecular Weight: 334.347
• Mol File: 6619-07-4.mol

Chemical Properties

• CAS DataBase Reference: Toluene-4-sulfonic acid (2S,3S,4S,5S)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Toluene-4-sulfonic acid (2S,3S,4S,5S)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester(6619-07-4)
• EPA Substance Registry System: Toluene-4-sulfonic acid (2S,3S,4S,5S)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester(6619-07-4)

Safety Data

• Hazardous Substances Data: 6619-07-4(Hazardous Substances Data)

Upstream product

• 70932-38-6 1,2:3,4-di-O-isopropylidene-6-O-(p-toluenesulfonyl)-α-L-galactopyranose 
• 4478-43-7 (1,2:3,4-di-O-isopropylidene-6-O-(p-toluensulfonate))-D-galactopiranose 
• 655-45-8 L-gulose 
• 98-59-9 p-toluenesulfonyl chloride 
• 2280-44-6 D-Glucose 
• 530-26-7 D-Mannose 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 

Downstream Products

• 138332-00-0 6-azido-6-deoxy-D-mannopyranose 
• 87303-54-6 1,2,3,4-Tetra-O-acetyl-6-O-(p-tolylsulfonyl)-β-D-mannopyranose 
• 121424-20-2 1,2,3,4-tetra-O-acetyl-6-(4-methylbenzenesulfonate)-α-D-mannopyranose 
• 13242-55-2 2,3,4-tri-O-acetyllevoglucosan 
• 20113-43-3 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose 
• 1025959-81-2 tert-Butyl-[(2R,5R)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-[1,3]oxathiolan-2-ylmethoxy]-diphenyl-silane 
• 139757-71-4 (+)-(1'S,2R,5R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(1',2'-dihydroxyethyl)-1,3-oxathiolane 
• 139757-69-0 1,2,3,4-tetra-O-acetyl-6-O-tosyl-L-gulopyranoside 
• 95118-61-9 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α,β-D-glucopyranose 
• 498-07-7 levoglucosan 
• 103042-48-4 3,4-di-O-acetyl-2,6-di-O-tosyl-α/β-D-glucopyranose 
• 14440-51-8 1,6-anhydro-2,3-O-isopropylidene-β-D-mannopyranose 
• 136794-40-6 (-)-4-O-benzoyl-2,3-O-isopropylidene-1,6-dideoxy-1,6-thioanhydro-D-mannopyranose 
• 136794-41-7 (-)-4-O-benzoyl-1,6-dideoxy-1,6-thioanhydro-D-mannopyranose 

Relevant articles and documents

D - And L -Mannose-Containing glyco-Oligoamides Show Distinct Recognition Properties When Interacting with DNA

Mannose glyco-oligoamide β-D-Man-Py-γ-Py-Ind (β-D-Man, 1) and two new glyco-oligoamides, β-L-Man-Py-γ-Py-Ind (β-L-Man, 2) and 6-deoxy-β-D-Man-Py-γ-Py-Ind (6-deoxy-β-D-Man, 3), have been designed and synthesized to investigate the role of hydrogen-bonding

Phosphatidylinositol 3-phosphate mimics based on a sulfoquinovose scaffold: Synthesis and evaluation as protein kinase B inhibitors

New sulfoquinovose analogues of phosphatidylinositol 3-phosphate have been synthesised based on a sulfoquinovose scaffold as potential protein kinase B (PKB) inhibitors. The synthetic strategy involved the introduction into glucose of a thioacetate group at the 6-position and of an azide group at the anomeric position as precursors of the sulfonate and phosphoramidate moieties present in the final compounds. The synthesised compounds were tested in vitro on isolated PKB by means of ELISA assays and for their anti-proliferative activity against the human ovarian carcinoma cell line IGROV-1. Sulfoquinovose derivatives 2b and 2c showed inhibitory activity in the low micromolar range.

Clustering of Escherichia coli type-1 fimbrial adhesins by using multimeric heptyl α- D -mannoside probes with a carbohydrate core

Heptyl α-D-mannoside (HM) is a strong inhibitor of the FimH lectin that mediates the initial adhesion of the uropathogenic Escherichia coli (E. coli) to the bladder cells. We designed a set of multivalent HM ligands based on carbohydrate cores with struct

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NOVEL 15O-LABELED MONOSACCHARIDE AND PRODUCING METHOD THEREOF

This invention relates to novel 15O-labeled monosaccharide useful for positron emission tomography (PET) and producing method thereof.

Chemoenzymatic synthesis of CMP-sialic acid derivatives by a one-pot two-enzyme system: Comparison of substrate flexibility of three microbial CMP-sialic acid synthetases

Three microbial CMP-sialic acid synthetases were cloned from Neisseria meningitidis, Streptococcus agalactiae, and Escherichia coli, respectively. Their activities in the production of CMP-sialic acid analogs were compared by HPLC analysis. The N. meningitidis synthetase was used in the preparative synthesis of eight CMP-sialic acid derivatives in a one-pot two-enzyme system. Three C terminal His6-tagged recombinant microbial CMP-sialic acid synthetases [EC 2.7.7.43] cloned from Neisseria meningitidis group B, Streptococcus agalactiae serotype V, and Escherichia coli K1, respectively, were evaluated for their ability in the synthesis of CMP-sialic acid derivatives in a one-pot two-enzyme system. In this system, N-acetylmannosamine or mannose analogs were condensed with pyruvate, catalyzed by a recombinant sialic acid aldolase [EC 4.1.3.3] cloned from E. coli K12 to provide sialic acid analogs as substrates for the CMP-sialic acid synthetases. The substrate flexibility and the reaction efficiency of the three recombinant CMP-sialic acid synthetases were compared, first by qualitative screening using thin layer chromatography, and then by quantitative analysis using high performance liquid chromatography. The N. meningitidis synthetase was shown to have the highest expression level, the most flexible substrate specificity, and the highest catalytic efficiency among the three synthetases. Finally, eight sugar nucleotides, including cytidine 5′-monophosphate N-acetylneuraminic acid (CMP-Neu5Ac) and its derivatives with substitutions at carbon-5, carbon-8, or carbon-9 of Neu5Ac, were synthesized in a preparative (100-200 mg) scale from their 5- or 6-carbon sugar precursors using the N. meningitidis synthetase and the aldolase.

A practical large-scale access to 1,6-anhydro-β-D-hexopyranoses by a solid-supported solvent-free microwave-assisted procedure

Microwave irradiation of 6-O-tosyl or 2,6-di-O-tosyl peracetylated hexopyranoses absorbed on basic alumina in a dry medium afforded the corresponding 1,6-anhydro-β-D-hexopyranoses. A direct access to 1,6:3,4-dianhydro-β-D-altropyranose (16) from D-glucose is also described.

Studies related to synthesis of glycophosphatidylinositol membrane-bound protein anchors. 6. Convergent assembly of subunits

Glycophosphatidylinositol anchors of membrane-bound proteins are thought to comprise a common pentasaccharide core containing mannan, glucosamine, and inositol residues. A synthetic route to this core is described. In addition, the complete heptasaccharide moiety of the rat brain Thy-1 membrane anchor, the first mammalian membrane anchor to be characterized, has been synthesized. In the case of the Thy-1 anchor, the synthetic plan is based on three building blocks comprising glucosamine-inositol, galactosamine-mannose, and trimannan residues. Although glycosyl donors other than n-pentenyl glycosides (NPGs) have been used in preparing each of these building blocks, the final assembly of the heptasaccharide utilizes NPGs as the only glycosyl donors. The mildness of the conditions for these coupling reactions has allowed us to make provisions for subsequent installation of the three phosphodiester units.

Asymmetric Synthesis and Biological Evaluation of β-L-(2R,5S)- and α-L-(2R,5R)-1,3-Oxathiolane-Pyrimidine and -Purine Nucleosides as Potential Anti-HIV Agents

In order to study the structure-acivity relationships of L-oxathiolanyl nucleosides as potential anti-HIV agents, a series of enantiomerically pure L-oxathiolanyl pyrimidine and purine nucleosides were synthesized and evaluated for anti-HIV-1 activity in human peripheral blood mononuclear (PBM) cells.The key intermediate 8 was synthesized starting from L-gulose via 1,6-thiaanhydro-L-gulopyranose.The acetate 8 was condensed with thymine, 5-substituted uracils and cytosines, 6-chloropurine, and 6-chloro-2-fluoropurine to give pyrimidine and purine nucleosides.Upon evaluation of these final nucleosides, the 5-fluorocytosine derivative 51 was found to be the most potent compound among those tested.In the case of 5-substituted cytosine analogues, the antiviral potency was found to be in the following decreasing order: cytosine (β-isomer) > 5-iodocytosine (β-isomer) > 5-fluorocytosine (α-isomer) > 5-methylcytosine (α-isomer) > 5-methylcytosine (β-isomer) > 5-bromocytosine (β-isomer) > 5-chlorocytosine (β-isomer).Among the thymine, uracil, and 5-substituted uracil derivatives, thymine (α-isomer) and uracil (β-isomer) derivatives exhibited moderate anti-HIV activity.In the purine series, the antiviral potency is found to be in the following decreasing order: adenine (β-isomer) > 6-chloropurine (β-isomer) > 6-chloropurine (α-isomer) > 2-NH2-6-Cl-purine (β-isomer) > guanine (β-isomer) > N6-methyladenine (α-isomer) > N6-methyladenine (β-isomer).The cytotoxicity was also determined in human PBM cells as well as Vero cells.None of the synthesized nucleosides was toxic up to 100 μ in PBM cells.

2,3,4-Tri-O-acetyl-1,6-anhydro-β-D-mannopyranose, an artifact produced during carbohydrate analysis. A total synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-β-D-mannofuranose

This study confirms that 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-mannopyranose is an artifact produced during carbohydrate analysis. A new synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-β-D-mannofuranose is also described, and a novel dimer, 1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-5,5'-di-O-(1-methoxy ethyl)-di-α-D-mannofuranose, has been isolated. The structure of the dimer is confirmed by X-ray analysis of a derivative, 1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-di-α-D-mannofuranos e. This study confirms that 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-mannopyranose is an artifact produced during carbohydrate analysis. A new synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-β-D-mannofuranose is also described, and a novel dimer, 1,6′:6,1′- dianhydro-2,3:2′,3′-di-O- isopropylidene-5,5′-di-O-(1-methoxyethyl)-di-α-D- mannofuranose, has been isolated. The structural of the dimer is confirmed by X-ray analysis of a derivative, 1,6′:6, 1′-dianhydro-2,3:2′,3′-di-O-isopropylidene- di-α-D-mannofuranose.