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The syntheses of 44 1-carbamates from six different 1-O-unprotected carbohydrate derivatives (compounds 1-6), representing typical protecting pattern in glycoside synthesis, are described. The carbamate function is N-unsubstituted (compounds 1b-6b), mono- (compounds a: N-trichloroacetyl, c: N-monochloroacetyl, d: N-acetyl, e: N-ethyl, f: N-allyl, g: N-phenyl) or disubstituted (compounds h: imidazolyl, i: N-diethyl, j: N-diphenyl). Additionally, three N-chlorosulfonyl carbamates are synthesized and used as intermediates for the synthesis of N-unsubstituted compounds b. The accessibility of these compounds is described and compared. Some of the carbamates (1, 4, 5a-j) are used as model compounds for systematic investigations in glycoside syntheses. Selected experimental data (reaction conditions, anomeric ratios, rotation values, selected NMR data) are tabulated.

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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Process for the preparation of protected mono-sugar and oligo-sugar halides

The reaction of protected monosaccharides or oligosaccharides or protected monosaccharide and oligosaccharide derivatives containing an anomeric hydroxyl group with secondary alpha-haloenamines affords high yields of protected glycosyl halides, which are valuable intermediates for the introduction of sugar groups in the synthesis of oligosaccharides, glycolipids or glycopeptides.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Reliable synthesis of various nucleoside diphosphate glycopyranoses

A reliable and high yielding synthetic pathway for the synthesis of the biologically highly important class of nucleoside diphosphate sugars (NDP-sugars) was developed by using various cycloSal-nucleotides 1 and 9 as active ester building blocks. The reaction with anomerically pure pyranosyl1-phosphates 2 led to the target NDP-sugars 20-45 in a nucleophilic displacement reaction, which cleaves the cycloSal moiety in anomerically pure forms. As nucleosides cytidine, uridine, thymi-dine, adenosine, 2?-deoxy-guanosine and 2?,3?-dideoxy-2?,3?- didehydrothymidine were used while the phosphates of D-glucose, D-galactose, D-mannose, DNAc-glucosamine, D-NAc-galactosamine, D-fucose, L-fucose as well as 6deoxy-D-gulose were introduced.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Oxidative deprotection of allyl glycosides

Allyl glycosides can be deprotected under the condition of the Kharasch- Sosnovsky reaction and by photoinduced reaction with di-(t)butylperoxide in the presence of bromotrichloromethane.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Interested yet? Keep reading other articles of 10343-06-3!, Computed Properties of C14H20O10

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Synthesis, gp120 binding and anti-HIV activity of fatty acid esters of 1,1-linked disaccharides

Inspired by the anti-human immunodeficiency virus (HIV) activity of analogues of beta-galactosylceramide (GalCer), a set of mono- and di-saccharide fatty acid esters were designed as GalCer mimetics and their binding to the V3 loop peptide of HIV-1 and anti-HIV activity evaluated. 1,1-linked Gal-Man and Glu-Man disaccharides with an ester on the Man subunit bound the V3 loop peptide and inhibited HIV infectivity in single round infection assays with the TZM-bl cell line. IC50’s were in the 50 muM range with no toxicity to the cells at concentrations up to 200 muM. These compounds appear to inhibit virus entry at early steps in viral infection since they were inactive if added post viral entry. Although these compounds were found to bind to the V3 loop peptide of gp120, it is not clear that this interaction is responsible for their anti-HIV activity because the relative binding affinity of closely related analogues did not correlate with their antiviral behavior. The low cytotoxicity of these 1,1-linked disaccharide fatty acid esters, combined with the easy accessibility to structurally diverse analogues make these molecules attractive leads for new topical anti-viral agents.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Catechin Glucosides: Occurrence, synthesis, and stability

Catechins are flavonoids with suggested health benefits, but are unstable during storage, processing and, after ingestion, during gut transit. We hypothesized that catechin glucosidos, which occur in various plants, could be more stable than unsubstituted catechin, and additionally be deglucosylated in the gut and so act to deliver catechin in a form able to be absorbed. (+)-Catechin O-glucosides from various sources have been used in the course of this investigation. (+)-Catechin 3′-O-beta-D-glucopyranoside (C3’G), (+)-catechin 5-O-beta-D-glucopyranoside (C5G), and (+)-catechin 3-O-beta-D-glucopyranoside (C3G) were chemically synthesized. (+)-Catechin 4′-O-beta-D-glucopyranoside (C4’G) and (+)-catechin 7-O-beta-D-glucopyranoside (C7G) were prepared enzymically using preparations from lentil and barley. In general, but with some exceptions, the (+)-catechin glucosidos were more stable between pH 4 and 8 than (+)-catechin, with C3’G exhibiting greatest stability. The intestinal metabolism of (+)-catechin and all (+)-catechin glucosides in the gut was determined by perfusion of rat intestine in vivo. C3’G and C5G were extensively deglycosylated in the gut, and C3’G showed greatest apparent “absorption” as calculated by the difference between effluent and influent. The results show the potential of catechin glucosides, especially C3’G, as more stable prescursors of catechin.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Ab initio analysis of the interaction of CO2 with acetylated d -glucopyranose derivatives

Peracetylated d-glucopyranose has a high solubility in CO2 and can be a promising phase-change physical solvent or absorbent for CO2, as reported recently. However, peracetylated d-glucopyranose is unstable under acidic atmospheres, especially in sulfur-containing waste gases, and the possibly major decomposition products are 2,3,4,6-tetra-O-acetyl-d-glucopyranose, 1-thiol-d-glucopyranose tetraacetate, and 1-mercaptoethyl-d-glucopyranose tetraacetate. Therefore, it is highly interesting to investigate the interaction between CO2 and these three compounds using ab initio calculations, including geometry optimizations with HF/3-21G, B3LYP/6-31+G??and single-point energy calibration with MP2/aug-cc-pVDZ. The results indicate that the electrostatic interactions between the substrates and CO2 are mainly influenced by the interaction distance and the numbers of negative charge donors or the interacting pairs involved in the complex. It is furthermore found that DeltaE increases significantly if S and O atoms could interact with CO2 simultaneously. The binding energy is irrelevant if one considers the chemical environment of the O atom (i.e. OAc, OE or OS) or the S atom (i.e. SEt or SH), and the electronegativity difference between the S and O atoms. The three substrates studied are still excellent CO2-philes, although their average DeltaE (-20kJ/mol) is slightly lower than that of peracetylated d-glucose (-22kJ/mol), which has one more O atom that can interact with CO2. Therefore, the applications of carbohydrates can be expanded to include adsorbents for CO2, SO2 or both, and the functional groups attached to the carbohydrate can vary from those to the acetyl groups.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Synthesis and use of glycosyl phosphites: An effective route to glycosyl phosphates, sugar nucleotides, and glycosides

An efficient and convenient synthetic route to glycosyl phosphites and phosphates has been developed that uses dibenzyl N,N-diethylphosphoramidite as a phosphitylating reagent. Glycosyl phosphites and phosphates of 2-acetamido-2-deoxy-D-galactose (GalNAc) (29), 2-acetamido-2-deoxy-D-glucose (GlcNAc) (30), D-galactose (Gal) (31), D-glucose (Glc) (32), D-mannose (Man) (33), L-rhamnose (Rha) (34), L-fucose (Fuc) (35), and N-acetylneuraminic acid (NeuAc) (41) were prepared by this procedure. Compounds 29 and 30 were obtained as alpha anomers exclusively, whereas compounds 31, 32, and 41 were obtained as beta anomers, and compounds 33 and 34, as alpha anomers, predominately. The phosphates are useful for the synthesis of sugar nucleotides, and the phosphites are effective glycosylation reagents.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Total synthesis of three natural phenethyl glycosides

Phenethyl glycosides having phenolic or methoxy functions at benzene rings are substances widely occurring in nature. This kind of compounds has been shown to have anti-oxidant, anti-inflammatory, and anticancer activities. However, some of them are not naturally abundant, thus the synthesis of such molecules is desirable. In this paper, natural phenethyl glycosides 3 and 4 were first totally synthesized from easily available materials with overall yields of 50.5% and 40.1%, respectively. And a new synthetic route to obtain natural phenethyl glycoside 2 in 46.2% yield was also described.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Synthesis and antitumor activity of new shikonin glycosides

Eleven shikonin glycosides were synthesized and evaluated for their antitumor activity in vitro. Some of them were found to exhibit cytotoxic activities against both drug sensitive cell lines (K562, MCF-7 and HL60) and their drug resistant cell sublines (K562/ADR, MCF-7/ADR and HL60/ADR).

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics