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Design and synthesis of boron containing monosaccharides by the hydroboration of D-glucal for use in boron neutron capture therapy (BNCT)

Boron neutron capture therapy (BNCT) is one of the radiotherapies that involves the use of boron-containing compounds for the treatment of cancer. Boron-10 (10B) containing compounds that can accumulate in tumor tissue are expected to be suitable agents for BNCT. We report herein on the design and synthesis of some new BNCT agents based on a D-glucose scaffold, since glycoconjugation has been recognized as a useful strategy for the specific targeting of tumors. To introduce a boryl group into a D-glucose scaffold, we focused on the hydroboration of D-glucal derivatives, which have a double bond between the C1 and C2 positions. It was hypothesized that a C?B bond could be introduced at the C2 position of D-glucose by the hydroboration of D-glucal derivatives and that the products could be stabilized by conversion to the corresponding boronic acid ester. To test this hypothesis, we prepared some 2-boryl-1,2-dideoxy-D-glucose derivatives as boron carriers and evaluated their cytotoxicity and cellular uptake activity to cancer cells, especially under hypoxic conditions.

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Electrochemistry of chalcogenoglycosides. Rational design of iterative glycosylation based on reactivity control of glycosyl donors and acceptors by oxidation potentials

Electrochemical properties of various para-substituted phenylthio-, phenylseleno-, and phenyltelluroglucopyranosides bearing acetyl, benzoyl, and benzyl protecting groups have been investigated to estimate the reactivity of chalcogenoglycosides toward electrochemical glycosylations. The oxidation potential of the chalcogenoglycosides shows good correlation with the ionization potential of chalcogen atoms, and decreases in the order thio-, seleno-, and telluroglycosides. It is also affected by the para-substituents, and the substitution effect correlates very well with the HOMO energy of para-substituted benzenechalcogenol and with the Hammett sigmap+ value. Electrochemical glycosylation of telluroglycosides has been examined, and it was found that the use of an undivided cell is more effective than the use of a divided cell. Selective activation of the chalcogenoglycosides in bulk electrolysis based on their oxidation potentials has been examined, and the relative reactivity of the telluroglycosides can be estimated from their oxidation potentials. However, the relative reactivity of selenoglycosides in the preparative glycosylation was rather insensitive to the oxidation potential values.

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Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography

Solid-phase synthesis is a practical approach for simplifying the time-consuming and routine purification steps in the preparation of numerous naturally occurring molecules; however, studying such reactions is difficult due to the lack of a convenient monitoring method. By using thin-layer chromatography in conjunction with a photolabile linker on a resin, we developed a convenient and simple method for monitoring solid-phase reactions in real time by thin-layer chromatography. This method provides a user-friendly protocol for examining reaction conditions for solid-state syntheses.

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Tetrahydropyran – Wikipedia,
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Properties and Exciting Facts About 4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-¦Â-D-glucopyranoside

Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Product Details of 28244-94-2. In my other articles, you can also check out more blogs about 28244-94-2

A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 28244-94-2, Name is 4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-¦Â-D-glucopyranoside, molecular formula is C21H26O9S. In a Patent£¬once mentioned of 28244-94-2, Product Details of 28244-94-2

NOVEL NEISSERIA MENINGITIDIS SEROGROUP Y OLIGOMER AND PROCESS FOR SYNTHESIZING THEREOF

The present invention relates to novel oligomers of Neisseria meningitidis serogroup Y capsular polysaccharide repeating unit (Men-Y oligomers) and process for synthesizing novel Men- Y oligomers. In particular, the present invention relates to the chemical synthesis of the tetramer of Men- Y capsular polysaccharide repeating unit capable of being used as a candidate in the development of semisynthetic or fully synthetic conjugate vaccine against meningococcal serogroup Y bacterial infection.

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Programmable one-pot oligosaccharide synthesis

In an effort to develop a broadly applicable approach to the facile one- pot synthesis of oligosaccharides, the reactivity of a number of p- methylphenyl thioglycoside (STol) donors which are either fully protected or have one hydroxyl group exposed has been quantitatively determined by HPLC. We have characterized and quantified the influence on reactivity of the structural effects of different monosaccharine cores and different protecting groups on each glycoside donor. In addition, we have established a correlation between glycosyl donor reactivity and the chemical shift of the anomeric proton by 1H NMR. Using the reactivity data, we have created a database of thioglycosides as glycosyl donors and demonstrated its utility in the easy and rapid one-pot assembly of various linear and branched oligosaccharide structures. In addition, we have developed the first computer program, OptiMer, for use as a database search tool and guide for the selection of building blocks for the one-pot assembly of a desired oligosaccharide or a library of individual oligosaccharides.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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A generalized procedure for the one-pot preparation of glycosyl azides and thioglycosides directly from unprotected reducing sugars under phase-transfer reaction conditions

Per-O-acetylated glycosyl azides and thioglycosides were prepared in excellent yield directly from unprotected reducing sugars through in situ generation of per-O-acetylated glycosyl bromides by a generalized one-pot procedure under phase-transfer conditions. Stereoselective products were formed with complete inversion at the anomeric centers of the glycosyl bromides to provide a general high-yielding procedure for the preparation of 1,2-trans-glycosyl azides and thioglycosides. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

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Tetrahydropyran – Wikipedia,
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Discovery of 4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-¦Â-D-glucopyranoside

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Mild and efficient hydrolysis of thioglycosides to glycosyl hemiacetals using N-iodosaccharin

A convenient methodology has been developed for the mild hydrolysis of thioglycosides to the corresponding hemiacetals using N-iodosaccharin without any requirement of co-activator. Most of the functional groups used for the protecting group manipulation of carbohydrates remain unaffected under the reaction conditions. Georg Thieme Verlag Stuttgart.

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Synthesis of thioglycosides in room temperature ionic liquid

An eco-friendly reaction for the preparation of thioglycosides has been developed using an ionic liquid as the solvent. Thioglycosides were obtained in excellent yields on treatment of per-O-acetylated sugar derivatives with thiols in the presence of boron trifluoride diethyl etherate in [Bmim][BF4] as solvent at 20C. Supplemental materials are available for this article. Go to the publisher’s online edition of Journal of Carbohydrate Chemistry to view the free supplemental file. Taylor & Francis Group, LLC.

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Tetrahydropyran – Wikipedia,
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The reactant in an enzyme-catalyzed reaction is called a substrate. Enzyme inhibitors cause a decrease in the reaction rate of an enzyme-catalyzed reaction.I hope my blog about 28244-94-2 is helpful to your research., Safety of 4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-¦Â-D-glucopyranoside

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Dual effect of synthetic aminoglycosides: Antibacterial activity against Bacillus anthracis and inhibition of anthrax lethal factor

Defence against bioterrorism: Recent events have created an urgent need for therapeutic strategies to treat anthrax, an infectious disease caused by the toxigenic bacterium Bacillus anthracis. A new class of aminoglycosides (see picture) are powerful inhibitors under physiological conditions of the anthrax lethal factor, which has a major role in the disease, and function simultaneously as antibiotics against B. anthracis. (Chemical Equation Presented).

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Total synthesis of mangiferin, homomangiferin, and neomangiferin

Total synthesis of mangiferin, homomangiferin, and neomangiferin, three C-glycosyl xanthone natural products with a wide spectrum of pharmacological effects, has been achieved starting from 2,3,4,6-tetra-O-benzyl-alpha/beta-d-glucopyranose. The key steps involve a stereoselective Lewis acid promoted C-glycosylation of protected phloroglucinol with tetrabenzylglucopyranosyl acetate and a highly regioselective base-induced cyclization for the construction of the core xanthone skeleton.

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Tetrahydropyran – Wikipedia,
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