Brief introduction of (2S,3R,4R,5S,6R)-6-(Acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride

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PERMEABLE GLYCOSIDASE INHIBITORS AND USES THEREOF

The present invention is directed to compounds and pharmaceutical formulations comprising these compounds which are useful as O-linked N-acetylglucosaminidase (O-GlcNAcase) inhibitors, and thus may be useful for the treatment of certain disorders such as Alzheimer’s disease including reducing NFTs and/or hyperphosphorylated tau. The invention is also directed to use of the compounds as O-GlcNAcase imaging agents.

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Tetrahydropyran – Wikipedia,
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SYNTHETIC OLIGOSACCHARIDES FOR STAPHYLOCOCCUS VACCINE

The present invention synthetic oligo-beta-(1?6)-glucosamine structures and a methodology which essentially allows for the synthesis of any oligo-beta-(1?6)-glucosamine species having a definite number of monosaccharide units, including a set pattern of acetylated and non- acetylated residues. The invention further provides antibodies to these synthetic oligo-beta-(1?6)-glucosamines as well as compositions thereof and methods for treating and preventing infections caused by bacteria expressing poly-beta-(1?6)-glucosamines, such as Staphylococcus aureus.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Differently glycosidated 2-amino-2-deoxy-D-glucopyranosiduronic acids as building blocks in peptide synthesis

Seven differently glycosidated sugar amino acids (SSAs) derived from glucosamine have been prepared. Following standard solution-phase peptide-coupling procedures, the glycosidated 2-amino-2-deoxy-D- glucopyranosiduronic acids were condensed with natural amino acids to furnish useful heterodi- and -trimeric building blocks to be used in peptide synthesis. Combinations of these building blocks yielded hetero-oligomeric peptides with two sugar amino acid units in different distances to each other. These were prepared to evaluate the influence of glycosidic side chains on the peptide backbone. Conformations of selected examples were examined by means of ROESY spectroscopy in combination with molecular dynamics (MD) simulations and circular-dichroism (CD) studies.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Discovery of (2S,3R,4R,5S,6R)-6-(Acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride

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Design, synthesis, and biological evaluation of 1,8-naphthyridine glucosamine conjugates as antimicrobial agents

In the quest for discovering potent antimicrobial agents with lower toxicity, we envisioned the design and synthesis of nalidixic acid-D-(+)-glucosamine conjugates. The novel compounds were synthesized and evaluated for their in vitro antimicrobial activity against Gram positive bacteria, Gram negative bacteria and fungi. Cytotoxicity using MTT assay over L6 skeletal myoblast cell line, ATCC CRL-1458 was carried out. In vitro antimicrobial assay revealed that 1-ethyl-7-methyl-4-oxo-N-(1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucopyranose-2-yl)-[1,8]-naphthyridine-3-carboxamide (5) and 1-ethyl-7-methyl-4-oxo-N-(2-deoxy-D-glucopyranose-2-yl)-[1,8]-naphthyridine-3-carboxamide(6) possess growth inhibitory activity against resistant Escherichia coli NCTC, 11954 (MIC 0.1589 mM) and Methicillin resistant Staphylococcus aureus ATCC, 33591 (MIC 0.1589 mM). Compound (5) was more active against Listeria monocytogenes ATCC 19115 (MIC 0.1113 mM) in comparison with the reference nalidixic acid (MIC 1.0765 mM). Interestingly, compound (6) had potential antifungal activity against Candida albicans ATCC 10231 (MIC <0.0099 mM). Remarkably, the tested compounds had low cytotoxic effect. This study indicated that glucosamine moiety inclusion into the chemical structure of the marketed nalidixic acid enhances antimicrobial activity and safety. I hope this article can help some friends in scientific research. I am very proud of our efforts over the past few months and hope to 10034-20-5, help many people in the next few years., Application of 10034-20-5

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Discovery of (2S,3R,4R,5S,6R)-6-(Acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride

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Synthesis of Novel Jusbetonin Analogues and Their Cytotoxicity against Tumor Cell

Six novel analogues of bioactive natural indolo[3,2-b]quinoline alkaloid glycoside jusbetonin were designed and synthesized, employing polyphosphoric acid mediated cyclization and two different amidation strategies on introduction of tetra-O-acetyl-beta-d-glucosamine to tetracyclic carboxylic acids.

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Tetrahydropyran – Wikipedia,
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Final Thoughts on Chemistry for 10034-20-5

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Synthesis and biological evaluation of ureido and thioureido derivatives of 2-amino-2-deoxy-D-glucose and related aminoalcohols as N-acetyl-beta-D-hexosaminidase inhibitors

Ureido and thioureido derivatives of 2-acetamido-2-deoxy-beta-D-glucose, 1-amino-1-deoxy-D-glucitol and 2-(2-aminoethoxy)ethanol were prepared as N-acetyl-beta-D-hexosaminidase (NAHase) inhibitors and were evaluated on Trichomonas vaginalis NAHase. Although none showed complete inhibition of the enzyme at 100 muM, 1-amino-1-deoxy-D-glucitol derivatives acted as competitive inhibitors of the NAHase of T. vaginalis. Copyright (C) 1998 Elsevier Science Ltd.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Synthesis of NAG-thiazoline-derived inhibitors for beta-N-acetyl-d-hexosaminidases

Abstract beta-N-Acetyl-d-hexosaminidases are responsible for the metabolism of glycoconjugates in diverse physiological processes that are important targets for medicine and pesticide development. Fourteen new NAG-thiazoline derivatives were synthesized by cyclization and click reaction using d-glucosamine hydrochloride as the starting material. All the compounds created were characterized by NMR and HRMS spectra. A preliminary bioassay, using four enzymes from two beta-N-acetyl-d-hexosaminidase families, showed that most of the compounds synthesized exhibit selective inhibition of GH84 beta-N-acetyl-d-hexosaminidase. Among the compounds tested, compounds 5a (IC50=12.6 muM, hOGA) and 5e (IC50=12.5 muM, OfOGA) proved to be a highly selective and potent inhibitor.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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1,8-NAPHTHYRIDINE GLUCOSAMINE DERIVATIVES, THEIR USE IN THE TREATMENT OF MICROBIAL INFECTIONS, AND A METHOD FOR PREPARATION

The present disclosure provides a compound of Formula (I) or any pharmaceutically acceptable salt thereof for use in treating a microbial infection in a subject, a method for preparing the same, and a pharmaceutical composition thereof: (I) wherein R1 may include hydrogen; alkyl; cycloalkyl; alkenyl; cycloalkenyl; alkynyl; aryl; or heteroaryl; R2, R3, R4 may independently include hydrogen; alkyl; cycloalkyl; alkoxy; aryloxy; heteroaryloxy; halogen; hydroxyl; cyano; or heteroaryl; R5, R6, R7, R8 may include free hydroxy groups; fully acylated hydroxy groups; or partially acylated hydroxy groups having the group R9-(C=O)-; and wherein R9 may include alkyl; substituted or unsubstituted aryl; or arylalkyl.

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Tetrahydropyran – Wikipedia,
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Extracurricular laboratory:new discovery of (2S,3R,4R,5S,6R)-6-(Acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride

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Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and alpha-hydroxy-beta-amino esters

A series of peracylated glycosamine-derived thioureas have been synthesized and their behavior as bifunctional organocatalysts has been tested in the enantioselective nucleophilic addition of formaldehyde tert-butyl hydrazone to aliphatic alpha-keto esters for the synthesis of tertiary azomethyl alcohols. Using the 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-beta-d-glucosamine derived 3,5-bis-(trifluoromethyl)phenyl thiourea the reaction could be accomplished with high yields (75-98%) and moderate enantioselectivities (50-64% ee). Subsequent high-yielding and racemization-free tranformations of both aromatic- and aliphatic-substituted diazene products in a one pot fashion provide a direct entry to valuable azoxy compounds and alpha-hydroxy-beta-amino esters.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Pd nanosized particles supported on chitosan and 6-deoxy-6-amino chitosan as recyclable catalysts for Suzuki-Miyaura and Heck cross-coupling reactions

Several chitosan and 6-deoxy-6-amino chitosan-Schiff base ligands (1-4) were prepared by condensation of either 2-pyridinecarboxaldehyde or 2-(diphenylphosphino)benzaldehyde with the amino group(s) on chitosan and its derivative (6-deoxy-6-amino chitosan). The supported ligands were reacted with [PdCl2(COD)] to form chitosan-supported PdII catalysts (5-8). All the supported catalysts were air- and moisture-stable and have been characterized using elemental analysis, ICP-MS, UV-vis, FT-IR, PXRD, TGA, 31P solid state NMR and TEM. As models for the heterogenized catalysts (5 and 6), mononuclear PdII complexes (9 and 10) were also prepared via the Schiff-base condensation reaction of 1,3,4,6-tetra-O-acetyl- beta-d-glucosamine hydrochloride to form 1,3,4,6-tetra-O-acetyl-beta-d- glucos-2-pyridylimine and 1,3,4,6-tetra-O-acetyl-beta-d-glucos-2- (diphenylphosphino)imine which were subsequently reacted with [PdCl 2(COD)]. Complexes (9 and 10) and their precursors were characterized by 1H and 31P NMR, UV-vis, FT-IR spectroscopy and elemental analysis. Catalytic Suzuki-Miyaura and Heck carbon-carbon cross-coupling reactions were carried out using the supported Pd catalysts and their mononuclear analogues. The immobilized and homogeneous catalysts showed high activity for both the Suzuki-Miyaura and Heck cross-coupling reactions in organic and aqueous media. Homogeneous catalysts (9 and 10) decomposed during the first run, while the supported catalysts could be recycled and reused up to five times.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics