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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Final Thoughts on Chemistry for (2S,3S,4S,5R,6R)-2-(Methoxycarbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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New approach in the synthesis of M6G

Morphine-6-glucuronide (M6G) is the primarily active metabolite of morphine, produced endogenously by the UGT enzyme, which displays analgesic activity. For this reason, M6G is a promising drug candidate for the treatment of severe pain. We described herein a new, efficient and scalable synthesis of M6G using dimorphinic derivatives. This preparation of M6G could be performed on multigram scale with good yield and high purity.

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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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Tetrahydropyran – Wikipedia,
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Facile Cu(OTf)2-Catalyzed Preparation of Per-O-acetylated Hexopyranoses with Stoichiometric Acetic Anhydride and Sequential One-Pot Anomeric Substitution to Thioglycosides under Solvent-Free Conditions

Solvent-free per-O-acetylation of hexoses with a stoichiometric amount of acetic anhydride employing 0.03 mol % Cu(OTf)2 proceeded in high yields (90-99%) at room temperature to give exclusively pyranosyl products as an anomeric mixture, the alpha/beta ratio of which was dependent on the temperature and amount of catalyst used. Sequential anomeric substitution with p-thiocresol in the presence of BF3¡¤etherate gave the thioglycosides, isolated exclusively or predominantly as one anomer in 66-75% yields.

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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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TMSBr-mediated solvent- and work-up-free synthesis of alpha-2-deoxyglycosides from glycals

The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly alpha-selective.

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An efficient synthesis of a hexasaccharide – The repeating unit of the exopolysaccharide from Cryptococcus neoformans serovar A

A general method for the synthesis of 2-xylose or glucuronic acid branched (1?3)-linked mannose oligosaccharides has been developed. As a typical example, the synthesis of the methyl glycoside of beta-D-GlcpA-(1?2)-alpha-D-Manp-(1?3)-[beta-D-Xylp- (1?2)-]alpha-D-Manp-(1?3)-[beta-D-Xylp-(1?2)-]alpha-D- Manp, the repeating unit of the exopolysaccharide from Cryptococcus neoformans serovar A, was achieved in a regio- and stereoselective manner.

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Neutral sphingomyelinase 2 inhibitors based on the 4-(1H-imidazol-2-yl)-2,6-dialkoxyphenol scaffold

Neutral sphingomyelinase 2 (nSMase2), a key enzyme in ceramide biosynthesis, is a new therapeutic target for the treatment of neurological disorders and cancer. Using 2,6-dimethoxy-4-[4-phenyl-5-(2-thienyl)-1H-imidazol-2-yl]phenol (DPTIP), our initial hit compound (IC50 = 30 nM) from nSMase2 screening efforts, as a molecular template, a series of 4-(1H-imidazol-2-yl)-2,6-dialkoxyphenol derivatives were designed, synthesized, and evaluated. Systematic examination of various regions of DPTIP identified the key pharmacophore required for potent nSMase2 inhibition as well as a number of compounds with the 4-(1H-imidazol-2-yl)-2,6-dialkoxyphenol scaffold with similar or higher inhibitory potency against nSMase2 as compared to DPTIP. Among them, 4-(4,5-diisopropyl-1H-imidazol-2-yl)-2,6-dimethoxyphenol (25b) was found to be metabolically stable against P450 metabolism in liver microsomes and displayed higher plasma exposure following oral administration as compared to DPTIP. Analysis of plasma samples identified an O-glucuronide as the major metabolite. Blockade of the phase II metabolism should further facilitate our efforts to identify potent nSMase2 inhibitors with desirable ADME properties.

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Simple and efficient per-O-acetylation of carbohydrates by lithium perchlorate catalyst

Lithium perchlorate is demonstrated to be a highly efficient and convenient catalyst for the per-O-acetylation of various saccharides with excellent yields. Graphical Abstract

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Tetrahydropyran – Wikipedia,
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