89615-45-2

Usage

Uses

Used in Organic Synthesis:
2,3,5-Tri-O-benzyl-D-ribofuranose is used as a key intermediate in organic synthesis for the preparation of complex organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure and reactivity allow for the formation of various derivatives and the construction of intricate molecular architectures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3,5-Tri-O-benzyl-D-ribofuranose is used as a building block for the synthesis of novel drug candidates and the modification of existing drugs to improve their pharmacological properties, such as potency, selectivity, and bioavailability. Its versatility in organic synthesis enables the development of innovative therapeutic agents with improved efficacy and safety profiles.
Used in Agrochemical Industry:
2,3,5-Tri-O-benzyl-D-ribofuranose is also utilized in the agrochemical industry for the synthesis of new pesticides, herbicides, and other crop protection agents. Its application in this field contributes to the development of more effective and environmentally friendly solutions for agricultural challenges.
Used in Specialty Chemicals:
In the specialty chemicals sector, 2,3,5-Tri-O-benzyl-D-ribofuranose serves as a versatile intermediate for the synthesis of various high-value compounds, such as fragrances, dyes, and functional materials. Its unique chemical properties and reactivity make it an essential component in the production of these specialty chemicals.

InChI:InChI=1/C26H28O5/c27-26-25(30-18-22-14-8-3-9-15-22)24(29-17-21-12-6-2-7-13-21)23(31-26)19-28-16-20-10-4-1-5-11-20/h1-15,23-27H,16-19H2/t23-,24-,25-,26?/m1/s1

Upstream product

• 131896-99-6 methyl 2,3,5-tri-O-benzyl-α-L-ribofuranoside 
• 100-39-0 benzyl bromide 
• 162491-62-5 (2S,3R,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol 
• 52689-55-1 methyl α-L-ribofuranoside 
• 41546-21-8 L-ribose 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 131897-00-2 1,3,4-tri-O-benzyl-D-ribitol 
• 197716-38-4 2,3,5-tri-O-benzyl-1-O-methyl-D-xylofuranoside 
• 60887-34-5 (2S,3R,4R,5R)-3,4,6-Tris-benzyloxy-2-[((E)-propenyl)oxy]-hexane-1,5-diol 
• 79083-40-2 2,3,5-tri-O-benzyl-1-O-methyl-α-D-xylofuranoside 
• 1824-96-0 methyl α-D-xylofuranoside 
• 87-72-9 D-Xylose 
• 1824-96-0 methyl xylofuranoside 
• 532-20-7 D-xylofuranose 

Downstream Products

• 131897-00-2 1,3,4-tri-O-benzyl-D-ribitol 
• 162491-51-2 2-[(1S,2R,3S,4S)-2,3,5-tris(benzyloxy)-1,4-dihydroxypent-1-yl]-N-triphenylmethylimidazole 
• 162438-92-8 2-[(1R,2R,3S,4S)-2,3,5-tris(benzyloxy)-1,4-dihydroxypent-1-yl]-N-triphenylmethylimidazole 
• 181863-14-9 (1S,2R,3S,4S)-2,3,5-Tris-benzyloxy-1-(2-trityl-2H-[1,2,4]triazol-3-yl)-pentane-1,4-diol 
• 162438-96-2 2-[(1S,2R,3S,4S)-2,3,5-tris(benzyloxy)-4-benzylsulfonyloxy-1-hydroxypent-1-yl]-N-triphenylmethylimidazole 
• 162438-94-0 (5R,6S,7S,8R)-6,7-bis(benzyloxy)-5-benzyloxymethyl-5,6,7,8-tetrahydro-8-hydroxyimidazo[1,2-a]pyridine 
• 162491-53-4 (5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-5,6,7,8-tetrahydro-8-hydroxyimidazo[1,2-a]pyridine 
• 162438-93-9 (5R,6S,7S,8R)-8-acetoxy-6,7-bis(benzyloxy)-5-benzyloxymethyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 
• 162491-52-3 (5R,6S,7S,8S)-8-acetoxy-6,7-bis(benzyloxy)-5-benzyloxymethyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 
• 162438-95-1 (5R,6S,7S,8S)-8-azido-6,7-bis(benzyloxy)-5-benzyloxymethyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 
• 188476-91-7 methyl (5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-5,6,7,8-tetrahydro-8-hydroxyimidazo[1,2-a]pyridine-2-acetate 
• 169134-62-7 (5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 
• 169134-65-0 (5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-2-bromo-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 
• 169134-64-9 (5R,6S,7S,8S)-6,7-bis(benzyloxy)-5-benzyloxymethyl-2,3-dibromo-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 

Relevant academic research and scientific papers

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

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.

PYRROLIDINE DERIVATIVES AS SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF

Disclosed are compounds of formula (I): or a pharmaceutically acceptable salt, derivative, solvate, isomer, tautomer, N-oxide, ester, prodrug, isotope or protected form thereof, which are of use as OGA inhibitors, for example in the treatment of various conditions and diseases, including neurodegenerative disorders.

PYRROLIDINE DERIVATIVES AS SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF

Disclosed are compounds of formula (I) or a pharmaceutically acceptable salt, derivative, solvate, isomer, tautomer, N-oxide, ester, prodrug, isotope or protected form thereof, which are of use as OGA inhibitors, for example in the treatment of various conditions and diseases, including neurodegenerative disorders