89887-98-9

Usage

Chemical structure

1,5-anhydro-3,4,6-tri-O-methyl-2-deoxy-D-lyxo-hex-1-enitol is a complex chemical compound with a unique structure, consisting of a hex-1-enitol core with three methyl groups and an anhydro bridge.

Derivative

It is a derivative of 2-deoxy-D-lyxo-hex-1-enitol, which is a type of sugar alcohol.

Methyl groups

The compound contains three methyl groups (-CH3) attached to the molecule, which contribute to its unique properties.

Anhydro bridge

The anhydro bridge (-O-) is a feature of the compound that connects two carbon atoms, resulting in the loss of a water molecule (dehydration).

Application in organic chemistry

This molecule is commonly used in organic chemistry as a building block for the synthesis of more complex compounds.

Pharmaceutical research

It is also used in pharmaceutical research for the development of new drug candidates and studying the behavior of organic molecules.

Structure-activity relationship studies

The unique properties of 1,5-anhydro-3,4,6-tri-O-methyl-2-deoxy-D-lyxo-hex-1-enitol make it an interesting target for chemical synthesis and structure-activity relationship studies in drug discovery and development.

Reactivity

The structure and reactivity of 1,5-anhydro-3,4,6-tri-O-methyl-2-deoxy-D-lyxo-hex-1-enitol make it a valuable tool for creating new drug candidates.

Stereochemistry

The compound has a specific stereochemistry, which is important for its biological activity and interactions with other molecules.

Solubility

Depending on its functional groups and molecular structure, the compound may have varying solubility properties in different solvents, which can be important for its use in chemical reactions and pharmaceutical formulations.

Upstream product

• 21193-75-9 D-galactal 
• 74-88-4 methyl iodide 
• 1071917-34-4 C₁₆H₂₄O₆S 
• 74-87-3 methylene chloride 
• 4098-06-0 triacetyl-D-galactal 

Downstream Products

• 1447908-95-3 (2R,3S,4R)-1,3,4-trimethoxy-5-(3-phenyl-4,5,6,7-tetrahydro-2-benzofuran-1-yl)-2-pentanol 

Relevant academic research and scientific papers

Palladium catalyzed stereocontrolled synthesis of C-aryl glycosides using glycals and arenediazonium salts at room temperature

A stereocontrolled synthesis of aryl-C-glycosides was achieved using glycals and aryldiazonium salts in the presence of palladium acetate. A wide range of glycals including d-glucal, d-galactal, l-rhamnal, d-xylal and d-ribal underwent C-arylation at the anomeric carbon in the presence of different aryldiazonium tetrafluoroborates and gave synthetically useful 2,3-deoxy-3-keto-α-aryl-C-glycosides in good to excellent yields. Broad substrate scope, simple operation and room temperature reactions make this protocol very attractive in organic synthesis.

Ir(I)-Catalyzed C?H Glycosylation for Synthesis of 2-Indolyl-C-Deoxyglycosides

The construction of 2-deoxy-C-glycosides has gradually become a hotspot of carbohydrate chemistry in recent years. In this work, we present an efficient, regioselective, stereoselective and widely applicable strategy for the synthesis of 2-indolyl-C-deoxyglycosides via Ir(I)-catalyzed, pyridine-group-directed C?H functionalization. This method exhibits high tolerance for the functional groups of indoles and the protecting groups of carbohydrates. Moreover, this protocol has good stereoselectivity and mainly produces β-configuration products. Gram-scale synthesis and several practical transformations were conducted for further applications. Meantime, we also explored the mechanism of this method and proposed a catalytic cycle. (Figure presented.).

Direct C-H Trifluoromethylation of Glycals by Photoredox Catalysis

A mild, efficient, and practical transformation for the direct C-H trifluoromethylation of glycals under visible light has been reported for the first time. This reaction employed fac-Ir3+(ppy)3 as the photocatalyst, Umemoto's reagent as the CF3 source, and a household blue LED or sunlight as the light source. Glycals bearing both electron-withdrawing and -donating protective groups performed this reaction smoothly. This visible light-mediated trifluoromethylation reaction was highlighted by the trifluoromethylation of the biologically important Neu2en moiety.

α-Selective organocatalytic synthesis of 2-deoxygalactosides

Alpha rules: A thiourea acts as an efficient organocatalyst for the glycosylation of protected galactals to form oligosaccharides containing a 2-deoxymonosaccharide moiety (see scheme). The reaction is highly stereoselective for α-linkages and proceeds by way of a syn-addition mechanism. Copyright

Fluorine-directed β-galactosylation: Chemical glycosylation development by molecular editing

Validation of the 2-fluoro substituent as an inert steering group to control chemical glycosylation is presented. A molecular editing study has revealed that the exceptional levels of diastereocontrol in glycosylation processes by using 2-fluoro-3,4,6-tri-O-benzyl glucopyranosyl trichloroacetimidate (TCA) scaffolds are a consequence of the 2R,3S,4S stereotriad. This study has also revealed that epimerization at C4, results in a substantial enhancement in β-selectivity (up to β/α 300:1). Copyright

Synthesis of glycal-based chiral benzimidazoles by VO(acac) 2-CeCl3 combo catalyst and their self-aggregated nanostructured materials

(Figure Presented) VO(acac)2-CeCl3 combo catalyst has been developed for chemoselective cyclocondensation cum oxidation under mild reaction conditions toward synthesis of a new class of optically pure compounds, 2-(2′-C-3′,4′,6′-tri-O-benzyl/methyl-glycal)-1H- benzimidazoles. It involves an operationally simple synthetic protocol efficient for the syntheses of a wide range of chiral benzimidazoles in high yields without formation of undesired 1,2-disubstituted and pseudoglycal byproducts. Vanadium(V) is found as active oxidant for the chemical processes which is investigated by UV absorption spectroscopy. Highly ordered one-dimensional low molecular mass organic nanostructured materials are fabricated by nanocrystallization of the chiral nanoscale building blocks. Theoretical calculation by the B3LYP/6-31G** level of theory of the glycal-based chiral benzimidazoles shows out of planar geometry of the 1H-anthra[1,2-d] imidazole-6,11-dione moiety, which is responsible for the strong self-aggregation to generate ultralong nanostructured materials. We have also found nice agreement between the theoretical results with the experimental observation in 2D-NOESY experiments. The photophysical property of the solid nanostructured materials is also reported. 2009 American Chemical Society.

Synthesis of pyranoid and furanoid glycals from glycosyl sulfoxides by treatment with organolithium reagents

Glycosyl sulfoxides can be conveniently transformed into pyranoid or furanoid glycals by treatment with organolithium reagents. The more likely reaction pathway involves a sulfoxide/metal exchange reaction to generate a glycosyllithium derivative that und

Remarkable oxidation stability of glycals: Excellent substrates for cerium(IV)-mediated radical reactions

The remarkable stability of glycals under oxidative conditions becomes apparent by their redox data in solution, computed HOMO energies, and behavior on the addition of electrophilic radicals generated in the presence of cerium(IV) ammonium nitrate. Oxida

Direct one-pot conversion of acylated carbohydrates into their alkylated derivatives under heterogeneous reaction conditions using solid NaOH and a phase transfer catalyst

A convenient one-pot protocol for the direct conversion of acyl-protected carbohydrates into their alkylated counterparts has been developed by using alkyl halides in the presence of solid sodium hydroxide and a phase transfer catalyst. These economically

THE ALKYLATION AND ACYLATION OF GLYCALS VIA AN INITIALIZING ELECTROCHEMICAL STEP

The method of electrochemically induced formation of ether and ester derivatives of saturated mono- and disaccharides was applied to 1,2-unsaturated monosaccharides (D-glycals).The influence of the supporting electrolyte on the product distribution was investigated by variation of the cation.To provide data for comparison, alkylation was also carried out chemically in the presence of different bases, e.g.LiH and NaH.