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Synthetic glycosides containing two isosteviol fragments functionalized with D-glucopyranose

The synthesis of isosteviol (16-oxo-ent-beyeran-19-oic acid) glycosides in which two isosteviol fragments functionalized with tetra-O-acetyl-D- glucopyranose are linked through a diester spacer is described for the first time.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Directed, Iterative, Stereoselective Synthesis of Oligosaccharides by Use of Suitably 2-O-Substituted 2-Pyridyl 1-Thioglycopyranosides on Activation by Methyl Iodide

The title synthesis is described by the proven methyl iodide activation procedure to obtain the alpha-linked oligosaccharides.Key words: Reiterative alpha-glycosidation; 2-pyridyl-1-thioglycopyranosides; armed-disarmed phenomena

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Synthesis of glycosyl phosphates and azides

Anomerically enriched diphenyl hexopyranosyl phosphate triesters have been prepared from O-alkyl and -acylated hexopyranoses, using diphenyl chlorophosphate and 4-N,N-dimethylaminopyridine. Glycosyl phosphate triesters of D-gluco-, D-galacto-, D-manno, 2-acetamido-2-deoxy-D-gluco-, L-fuco-, and L-rhamno-pyranosyl derivatives have been obtained by this procedure. At temperatures 0 and above, and under thermodynamic control, diphenyl glycosyl phosphates cis to the pyranosyl C-2 substituent are formed predominantly, whereas at low temperatures and under kinetic control, glycosyl phosphate triesters having 2-trans stereochemistry are obtained. The beta-glycosyl phosphate triesters of D-glucose and D-galactose derivatives are unstable and undergo anomerization to the alpha-glycosyl phosphate triesters, in contrast to the stable beta-phosphate derivatives of L-rhamnose and D-mannose. These phosphate triesters have been deprotected to glycosyl phosphate triethylammonium salts, suitable for the preparation of other key biological derivatives, such as nucleotide sugars. In addition, the diphenyl phosphate groups at the anomeric center have been displaced by azide togive the glycosyl azides, key intermediates in the synthesis of glycosyl amino acids. Anomerically enriched diphenyl hexopyranosyl phosphate triesters have been prepared from O-alkyl and -acrylated hexopyranoses, using diphenyl chlorophosphate and 4-N,N-dimethylaminopyridine. Glycosyl phosphate triesters of D-gluco-, D-galacto-, D-manno, 2-acetamido-2-deoxy-D-gluco-, L-fuco-, and L-rhamno-pyranosyl derivatives have been obtained by this procedure. At temperatures 0 and above, and under thermodynamic control, diphenyl glycosyl phosphates cis to the pyranosyl C-2 substituent are formed predominantly, whereas at low temperatures and under kinetic control, glycosyl phosphate triesters having 1,2-trans stereochemistry are obtained. The beta-glycosyl phosphate triesters of D-glucose and D-galactose derivatives are unstable and undergo anomerization to the alpha-glycosyl phosphate triesters, in contrast to the stable beta-phosphate derivatives of L-rhamnose and D-mannose. These phosphate triesters have been deprotected to glycosyl phosphate triethylammonium salts, suitable for the preparation of other key biological derivatives, such as nucleotide sugars. In addition, the diphenyl phosphate groups at the anomeric center have been displaced by azide to give the glycosyl azides, key intermediates in the synthesis of glycosyl amino acids.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Synthesis, chemical characterization and antimicrobial activity of new acylhydrazones derived from carbohydrates

A new series of glycosylated acylhydrazones was synthesized and all the chemical structures were confirmed by High Resolution Mass Spectrometry (HRMS), 1H and 13C Nuclear Magnetic Resonance (1H-NMR; 13C-NMR) and Fourier Transform Infrared (FTIR) spectroscopy methods. The mass accuracy between the calculated and found values observed in HRMS analyses were near or lower than 5 ppm, which are acceptable for proposing a molecular formula using this technique. All of the synthesized compounds were screened for their antibacterial, antifungal and antiviral activities. Five compounds (12, 13, 14, 16 and 19) exerted a modest antifungal activity against the strains evaluated. Derivative 14 showed fungicidal activity against Candida glabrata at 173.8 muM and saccharide unit contributed to the increase of the antifungal potential against this strain. New chemical manipulation of derivative 14 can make it possible to obtain new potentially antimicrobial agents.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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NIS/TFA: a general method for hydrolyzing thioglycosides

A variety of thioglycosides are chemoselectively hydrolyzed to the corresponding 1-hydroxy glycosides using equimolar amounts of NIS/TFA as promoter systems.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Efficient method for the one-pot azidation of alcohols using bis(p-nitrophenyl) phosphorazidate

The direct stereoselective conversion of various alcohols and hexopyranoses into the corresponding alkyl azides and glycosyl azides, respectively, is efficiently accomplished by using bis(p-nitrophenyl) phosphorazidate and DBU.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Ruthenium-catalysed cross metathesis binding of functionalized olefins to polystyrene resin via a novel allylsilyl linker suitable for electrophilic cleavage

1% Divinylbenzene-crosslinked allyldimethylsilyl polystyrene 1 undergoes highly efficient ruthenium-catalysed cross-metathesis with functionalized terminal olefins and allows electrophilic cleavage of the resulting functionalized allylsilane.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Generation of near-enantiopure alpha-alkyl alpha-formyl alpha-hydroxy ketones/esters and their interception with ethoxycarbonylmethylenetriphenylphosphorane

Two protocols for the generation of the (R)-enantiomers of alpha-alkyl alpha- formyl alpha-hydoxy ketones/esters in states of high enantiomeric purity are developed; the formyl functions of such compounds undergo Wittig condensations with ethoxycarbonylmethylenetriphenylphosphorane in dimethyl sulfoxide to afford the corresponding alkenes with high (E)- stereoselectivities and with e.e.s of 91-99%.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2-Aryl-1,3-dithiane 1-Oxide?

A new dehydrative glycosylation reaction has been established by capitalizing on the comproportionation reaction of 2-aryl-1,3-dithiane 1-oxides promoted by triflic anhydride (Tf2O). By wedding the high potency of thiophilic promoter system with the step efficiency of dehydrative glycosylation, this reagent underwent facile intermolecular oxothio acetalization with C1-hemiacetal donor to install a temporary leaving group, rendering a transient electrophilic center at the remote site to the anomeric position. The sulfenyl triflate tethered at the terminus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion, thereby facilitating the title glycosylation. Aside from accommodating broad range functional groups and inactive hemiacetal substrates, the present activation protocol also proved expedient for 1,3-diol protection. Most importantly, this method further provided a fresh perspective for the application of sulfur chemistry to carbohydrate chemistry.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Palladium(ll)-catalyzed transfer vinylation of protected monosaccharides

(Matrix presented) A method for the catalytic vinylation of protected monosaccharides bearing a single free hydroxyl function has been developed. Reaction of representative primary, secondary, and anomeric sugar hydroxyl functions with butyl vinyl ether as the reactant and solvent and (phen)Pd-(OAc)2 (phen = 1,10-phenanthroline ligand) as the catalyst gives the corresponding vinylated sugar products in 36-79% yield. The catalyst requires the presence of traces of oxygen in the reaction mixture to prevent decomposition to Pd(0).

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics