96192-07-3

Usage

Type of compound

furanose sugar derivative

Usage

organic synthesis, chemical intermediate in production of pharmaceuticals and agrochemicals

Characterized by

three benzyl groups attached to beta-L-arabino-furanose core

Unique properties

chemical and physical properties due to the presence of benzyl groups

Utilized in

development of novel drugs, advanced materials, and biochemical research

Potential

building block for complex molecular structures

Versatility

valuable tool for chemists in creating new compounds with specific properties and functions.

Upstream product

• 13039-64-0 (2S,3R,4R)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3,4-diol 
• 131615-65-1 methyl 2,3,5-tri-O-benzyl-α,β-L-arabinofuranoside 
• 100-39-0 benzyl bromide 
• 52689-55-1 methyl α-L-ribofuranoside 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 131897-00-2 1,3,4-tri-O-benzyl-D-ribitol 
• 79083-40-2 2,3,5-tri-O-benzyl-1-O-methyl-α-D-xylofuranoside 
• 51755-00-1 methyl 3-O-benzyl-3,5-O-isopropylidene-α-D-xylofuranoside 
• 892858-75-2 methyl 2-O-benzyl-D-xylofuranoside 
• 7045-40-1 Methyl 3,5-O-Isopropylidene-α-D-xylofuranoside 
• 79083-41-3 2,3,5-tri-O-benzyl-1-O-methyl-β-D-xylofuranoside 
• 41546-31-0 L-xylose 
• 100-44-7 benzyl chloride 
• 13039-67-3 (2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol 

Downstream Products

• 129926-97-2 2-(2',3',5'-tri-O-benzyl-α-L-arabinofuranosyl)-4,5-methylenedioxyphenol 
• 141062-53-5 Acetic acid (2S,3S)-1,2,4-tris-benzyloxy-3-formyloxy-butyl ester 
• 77871-03-5 ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,5-tri-O-benzyl-α-L-arabinofuranosyl)-L-hydroxyproline 
• 77871-03-5 2-N-(benzyloxycarbonyl)-4-O-(2,3,5-tri-O-benzyl-α-L-arabinofuranosyl)-L-hydroxyproline benzyl ester 
• 77871-03-5 2-N-(benzyloxycarbonyl)-4-O-(2,3,5-tri-O-benzyl-β-L-arabinofuranosyl)-L-hydroxyproline benzyl ester 
• 99388-77-9 Benzyl O-(2,3,4-tri-O-benzyl-α-L-arabinofuranosyl)-(1-3)-O-(2,4-di-O-benzyl-β-D-xylopyranosyl)-(1-4)-2,3-di-O-benzyl-α-D-xylopyranoside 
• 158012-86-3 (2S,3S,4S,5S)-1,3,4-Tris-benzyloxy-6-(diisopropyl-phenyl-silanyl)-hexane-2,5-diol 
• 913365-64-7 (2S,3S,4S)-2,3,5-Tris-benzyloxy-4-hydroxy-pentanal oxime 
• 98815-79-3 (2S,3S,3aS,9bR)-3-benzyloxy-2-benzyloxymethyl-3,3a,5,9b-tetrahydro-2H-furo<3,2-c><2>benzopyran 
• 86883-41-2 (2S,3S,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-fluoro-tetrahydro-furan 
• 129926-95-0 2-(2',3',5'-tri-O-benzyl-α-L-arabinofuranosyl)-5-hydroxyphenol 
• 129926-96-1 2-(2',3',5'-tri-O-benzyl-β-L-arabinofuranosyl)-5-hydroxyphenol 
• 222728-80-5 S-(2,3,5-tri-O-benzyl-α,β-L-arabinofuranosyl) O,O-diethyl phosphorodithioate 
• 304891-33-6 (10S)-2-tert-butyldimethylsilyl-5-(2',3',5'-tri-O-benzyl-L-arabinosyl)-N,N-dimethylimidazole-1-sulfonamide 

Relevant academic research and scientific papers

Surfactant-mediated thioglycosylation of 1-hydroxy sugars in water

Thioglycosides are an important class of sugars, since they can be used as non-ionic biosurfactants, biomimetic glycosides, and building blocks for carbohydrate synthesis. Previously, Br?nsted- or Lewis-acid-catalyzed dehydrative glycosylations between a 1-hydroxy sugar and a thiol have been reported to yield open-chain dithioacetal sugars as the major products instead of the desired thioglycosides. These dithioacetal sugars are by-products derived from the endocyclic bond cleavage of the thioglycosides. Herein, we report dehydrative glycosylation in water mediated by a Br?nsted acid-surfactant combined catalyst (BASC). Glycosylations between 1-hydroxy furanosyl/pyranosyl sugars and primary, secondary, and tertiary aliphatic/aromatic thiols in the presence of dodecyl benzenesulfonic acid (DBSA) provided the thioglycoside products in moderate to good yields. Microwave irradiation led to improvements in the yields and a shortening of the reaction time. Remarkably, open-chain dithioacetal sugars were not detected in the DBSA-mediated glycosylations in water. This method is a simple, convenient, and rapid approach to produce a library of thioglycosides without the requirement of anhydrous conditions. Moreover, this work also provides an excellent example of complementary reactivity profiles of glycosylation in organic solvents and water.

Anti-norovirus activity of C7-modified 4-amino-pyrrolo[2,1-f][1,2,4]triazine C-nucleosides

Synthetic nucleoside analogues characterized by a C–C anomeric linkage form a family of promising therapeutics against infectious and malignant diseases. Herein, C-nucleosides comprising structural variations at the sugar and nucleobase moieties were exam

Synthesis, Reactivity, and Stereoselectivity of 4-Thiofuranosides

Thiosugars, sugars that have their endocyclic oxygen substituted for a sulfur atom, have been used as stable bioisosteres of naturally occurring glycans because the thiosugar glycosydic linkage is supposed to be stabilized toward chemical and enzymatic hydrolysis. We have performed an in-depth investigation into the stability and reactivity of furanosyl thiacarbenium ions, by assessing all four diastereoisomeric thiofuranosides experimentally and computationally. We show that all furanosyl thiacarbenium ions react in a 1,2-cis-selective manner with triethylsilane, reminiscent of their oxo counterparts. The computed conformational space occupied by the thiacarbenium ions is strikingly similar to that of the corresponding furanosyl oxycarbenium ions, indicating that the stereoelectronic substituent effects governing the stability of furanosyl oxocarbenium ions and thiacarbenium ions are very similar. While the thio-ribo-furanose appears to be less reactive than its oxo counterpart, the thio-ara-, lyxo-, and xylo-furanosides appear to be more reactive than their oxygen equivalents. These differences are accounted for using the conformational preference of the donors and the carbocation intermediates. The lower reactivity of the thio-ribo furanosides in (Lewis) acid-mediated reactions and the similarity of the thia- and oxocarbenium ions make thio-ribo-furanosides excellent stabilized analogues of the naturally occurring ribo-furanose sugars.

Bicyclic 1-Azafagomine Derivatives: Synthesis and Glycosidase Inhibitory Testing

The synthesis of a series of 1-azafagomine derivatives that are tethered with five- and six-membered 1,2-annulated ring systems is described. These compounds were used in order to explore whether a hydrogen-bond acceptor group on the carbon atom corresponding to the glycosidic oxygen is able to interact with the catalytic acidic residue of β-glucosidase. The hydrogen-bond acceptor group was installed at various positions on the annulated ring system making it possible to study the effect of altering the position of this group.

Chemical Synthesis of Ketopentose-5-phosphates

A chemical synthesis of ketopentose-5-phosphates that are involved in the pentose phosphate pathway has been developed. The ketopentose phosphates, d-ribulose-5-phosphate and d-xylulose-5-phosphate, were prepared in five steps starting from known intermed

Synthesis of d -Fagomine and Its Seven- and Eight-Membered Higher-Ring Analogues, and the Formal Synthesis of (+)-Australine from l -Xylose-Derived Chiron

The synthesis of d-fagomine and its seven- and eight-membered higher-ring analogues from commercially available l-xylose is reported. The syntheses involve elaboration of a common alkenol precursor obtained from l-xylose-derived hemiacetal. The key steps

Synthesis and evaluation of: N -alkylated analogues of aza-galacto-fagomine-potential pharmacological chaperones for Krabbe disease

Seven novel alkylated or acylated analogues of hexahydropyridazine aza-galacto-fagomine (AGF) was prepared and studied as glycosidase inhibitors with the aim of increasing inhibitory potency and selectivity. The enzyme galactocerebrosidase, implicated in Krabbe disease, was found to be potently inhibited by n-butyl N2-alkylated AGF.

METHOD FOR PRODUCING THIOLANE SKELETON-TYPE GLYCOCONJUGATE, AND THIOLANE SKELETON-TYPE GLYCOCONJUGATE

PROBLEM TO BE SOLVED: To provide a simplified method for producing a synthetic intermediate of a thionucleoside in high yield under a moderate condition by a reaction to form a thiolane ring. SOLUTION: The present invention relates to a method for produci

Iodine monochloride (ICl) as a highly efficient, green oxidant for the oxidation of alcohols to corresponding carbonyl compounds

Iodine monochloride (ICl) was discovered to be a highly efficient, green oxidant, which can oxidize aldose hemiacetals, diarylmethanols, arylalkylmethanols, anddialkylmethanols to the corresponding aldose lactones, diarylmethanones, arylalkylmethanones, and dialkylmethanones, respectively, in high yields. ICl as a green, metal-free oxidant is characterized by mild reaction condition, short reaction time, good yield, and broad scope.

Azasugar inhibitors as pharmacological chaperones for Krabbe disease

Krabbe disease is a devastating neurodegenerative disorder characterized by rapid demyelination of nerve fibers. This disease is caused by defects in the lysosomal enzyme β-galactocerebrosidase (GALC), which hydrolyzes the terminal galactose from glycosphingolipids. These lipids are essential components of eukaryotic cell membranes: substrates of GALC include galactocerebroside, the primary lipid component of myelin, and psychosine, a cytotoxic metabolite. Mutations of GALC that cause misfolding of the protein may be responsive to pharmacological chaperone therapy (PCT), whereby small molecules are used to stabilize these mutant proteins, thus correcting trafficking defects and increasing residual catabolic activity in cells. Here we describe a new approach for the synthesis of galacto-configured azasugars and the characterization of their interaction with GALC using biophysical, biochemical and crystallographic methods. We identify that the global stabilization of GALC conferred by azasugar derivatives, measured by fluorescence-based thermal shift assays, is directly related to their binding affinity, measured by enzyme inhibition. X-ray crystal structures of these molecules bound in the GALC active site reveal which residues participate in stabilizing interactions, show how potency is achieved and illustrate the penalties of aza/iminosugar ring distortion. The structure-activity relationships described here identify the key physical properties required of pharmacological chaperones for Krabbe disease and highlight the potential of azasugars as stabilizing agents for future enzyme replacement therapies. This work lays the foundation for new drug-based treatments of Krabbe disease.