79083-42-4

Basic information

• Product Name: METHYL-D-ARABINOFURANOSIDE
• Synonyms: METHYL-D-ARABINOFURANOSIDE;D-Arabinofuranoside, Methyl;1-O-methyl-D-arabinofuranoside;(2R,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol;(2R,3S,4S)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3,4-diol
• CAS NO: 79083-42-4
• Molecular Formula: C₆H₁₂O₅
• Molecular Weight: 164.15648
• Mol File: 79083-42-4.mol

Chemical Properties

• Appearance: /
• Density: 1.40
• Storage Temp.: 2-8°C
• CAS DataBase Reference: METHYL-D-ARABINOFURANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL-D-ARABINOFURANOSIDE(79083-42-4)
• EPA Substance Registry System: METHYL-D-ARABINOFURANOSIDE(79083-42-4)

Safety Data

• Hazardous Substances Data: 79083-42-4(Hazardous Substances Data)

Usage

Uses

Used in Enzymatic Assays:
Methyl-D-arabinofuranoside is used as a substrate in enzymatic assays for studying various metabolic pathways, particularly those involving arabinose and its derivatives. It helps researchers understand the enzymatic reactions and mechanisms related to these pathways.
Used in Pharmaceutical Industry:
Methyl-D-arabinofuranoside is used in the synthesis of nucleosides and nucleotides, which are essential components of DNA and RNA. Its potential applications in the pharmaceutical industry include the development of new drugs targeting specific metabolic pathways or diseases.
Used in Biotechnology and Microbiology Research:
Methyl-D-arabinofuranoside has been studied for its potential as a carbon source for microbial growth. This makes it of interest in biotechnology and microbiology research, where it can be used to optimize microbial fermentation processes or to study the metabolic capabilities of various microorganisms.

Upstream product

• 67-56-1 methanol 
• 1114-34-7 D-lyxose 
• 532-20-7 D-lyxose 
• 50-69-1 D-ribose 
• 532-20-7 D-Ribose 
• 87-72-9 D-Xylose 
• 10323-20-3 D-Arabinose 
• 25545-03-3 β-D-arabinofuranose 
• 87-72-9 L-xylopyranose 
• 6748-95-4 β-D-arabinopyranose 
• 28697-53-2 D-arabinopyranose 
• 532-20-7 D-arabinofuranose 
• 75-36-5 acetyl chloride 
• 15135-34-9 D-arabinose dimethyl acetal 

Downstream Products

• 677299-16-0 (2R,3R,4R)-3,4-bis((2,4-dichlorobenzyl)oxy)-2-(((2,4-dichlorobenzyl)oxy)methyl)-5-methoxytetrahydrofuran 
• 108008-65-7 methyl 2,3,5-tri-O-(4-chlorobenzyl)-β-D-ribofuranoside 
• 64363-77-5 methyl 2,3,5-tri-O-benzyl-D-ribofuranoside 
• 67689-93-4 methyl 5-O-trityl-α-D-ribofuranoside 
• 37077-80-8 2,3,5-tri-O-acetyl-1-O-methyl-β-D-ribofuranose 
• 22860-91-9 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide 
• 162547-02-6 methyl 5-O-(t-butyldimethylsilyl)-2-O-cynnamoyl-3-O-(imidazol-1-yl)thiocarbonyl-β-D-ribofuranoside 
• 162678-62-8 methyl 5-O-(t-butyldimethylsilyl)-3-O-cinnamoyl-2-O-(imidazol-1-yl)thiocarbonyl-α-D-ribofuranoside 
• 137410-53-8 methyl 5-O-(t-butyldimethylsilyl)-3-O-cynnamoyl-2-O-(imidazol-1-yl)thiocarbonyl-β-D-ribofuranoside 
• 137410-60-7 methyl 5-O-(t-butyldimethylsilyl)-2-C-<(R)-carboxybenzylmethyl>-2-deoxy-3,2-γ-lactone-β-D-ribofuranoside 
• 137410-67-4 methyl 5-O-(t-butyldimethylsilyl)-3-O-cinnamoyl-2-deoxy-β-D-ribofuranoside 
• 69603-05-0 methyl-(O⁵-benzyl-O²,O³-carbonyl-β-D-ribofuranoside) 
• 81275-41-4 methyl 5-O-benzyl-2,3-O-isopropylidene-α-D-ribofuranoside 

Relevant articles and documents

Unexpected furanose/pyranose equilibration of N-glycosyl sulfonamides, sulfamides and sulfamates

De-protected arabino N-glycosyl sulfamides, sulfonamides and sulfamates were found to mutarotate and convert from the furanose to the thermodynamically more stable pyranose form in aqueous solution. The presence of a strongly electron withdrawing group in

Selective detection of epimeric pentose saccharides at physiological pH using a fluorescent receptor

Epimerisation between ribofuranose and arabinofuranose sugars is crucial in several biosynthetic pathways, but is typically challenging to monitor. Here, we have screened for fluorescent boronic acids that can be used as molecular probes for the specific detection of ribofuranose over arabinofuranose sugars in solution. We show excellent specificity of the fluorescent response of 3-biphenylboronic acid to ribofuranose at physiological pH. This provides a tool for in situ monitoring of carbohydrate modifying enzymes and provides a viable alternative to traditional radiolabelled assays.

Discovery of human hexosaminidase inhibitors by in situ screening of a library of mono- and divalent pyrrolidine iminosugars

Two libraries of mono- and dimeric pyrrolidine iminosugars were synthesized by CuAAC and (thio)urea-bond-forming reactions from the respective azido/aminohexylpyrrolidine iminosugar precursors. The resulting monomeric and dimeric compounds were screened f

Asymmetric Formal Synthesis of (-)-Swainsonine from Chiral-Pool Precursors d -Mannose and d -Arabinose

Carbohydrates have played an important role in organic synthesis. Since they contain many stereocenters, they have been widely used as chiral-pool starting materials. Herein, we report the asymmetric formal synthesis of (-)-swainsonine, which exhibits anticancer and immunosuppressive activities and inhibits lysosomal α-mannosidase activity, from D-mannose and D-arabinose. The synthesis utilized Zn-mediated Bernet-Vasella reaction, Horner-Wadsworth-Emmons olefination, and Grubbs olefin metathesis as key reactions.

Preparation method of compound with 3, 4-trans-3, 6-anhydrofuran hexose structure

The invention discloses a preparation method of a compound with a 3, 4-trans-3, 6-dehydrated furan hexose structure and a preparation method of the compound with the 3, 4-trans-3, 6-dehydrated furan hexose structure. The method comprises the following ste

MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF

The present disclosure provides oligomeric compounds comprising a modified oligonucleotide having at least one stereo-non-standard nucleoside. An oligomeric compound comprising a modified oligonucleotide consisting of 12-30 linked nucleosides, wherein at least one nucleoside of the modified oligonucleotide is a stereo-non-standard nucleoside; and wherein the oligomeric compound is selected from among an RNAi compound, a modified CRISPR compound, and an artificial mRNA compound.

Novel saccharide bio-based cyclic phosphorus/phosphonate as well as preparation method and application thereof

The invention discloses novel saccharide bio-based cyclic phosphorus/phosphonate as well as a preparation method and application thereof, and belongs to the field of compounds. The cyclic phosphorus/phosphonate is prepared by the following steps: reacting D-xylose with acetyl chloride to obtain an intermediate product, and then reacting with dichlorophosphate or phosphonic dichloride under the action of an acid-binding agent to obtain a target product. The preparation method is high in yield, simple in process, low in raw material cost and small in environmental pollution, and the prepared cyclic phosphorus/phosphonate flame retardant is outstanding in flame retardance and easy to industrialize.

Stereoselective Synthesis of Ribofuranoid exo-Glycals by One-Pot Julia Olefination Using Ribofuranosyl Sulfones

One-pot Julia olefination using ribofuranosyl sulfones is described. The α-anomers of the ribofuranosyl sulfones were synthesized with complete α-selectivity via the glycosylation of heteroarylthiols using ribofuranosyl iodides as glycosyl donors and the subsequent oxidation of the resulting heteroaryl 1-thioribofuranosides with magnesium monoperphthalate (MMPP). The Julia olefination of the α-ribofuranosyl sulfones with aldehydes proceeded smoothly in one pot to afford the thermodynamically less stable (E)-exo-glycals with modest-to-excellent stereoselectivity (up to E/Z = 94:6) under the optimized conditions. The E selectivity was especially high for aromatic aldehydes. In contrast, the (Z)-exo-glycal was obtained as the main product with low stereoselectivity when the corresponding β-ribofuranosyl sulfone was used (E/Z = 41:59). The remarkable impact of the anomeric configuration of the ribofuranosyl sulfones on the stereoselectivity of the Julia olefination has been rationalized using density functional theory (DFT) calculations. The protected ribose moiety of the resulting exo-glycals induced completely α-selective cyclopropanation on the exocyclic carbon-carbon double bond via the Simmons-Smith-Furukawa reaction. The 2-cyanoethyl group was found to be useful for the protection of the exo-glycals, as it could be removed without affecting the exocyclic C=C bond.

A stereoselective synthesis method for β-D-arabinofuran glycoside bonds

The present invention belongs to the field of natural oligosaccharide chain synthesis technology, specifically relates to a β-D- arabinofuran glycoside bond stereoselective synthesis method, the present invention to 2- O- benzyl-3,5-O- xylene -D- arabfura

BIOMARKER PANEL TARGETED TO DISEASES DUE TO MULTIFACTORIAL ONTOLOGY OF GLYCOCALYX DISRUPTION

The present disclosure provides biomarkers useful as companion diagnostics for detecting glycocalyx-based disease that is amenable to treatment using compounds designed for improving the condition of the glycocalyx and/or reducing inflammation and/or oxidative damage, as well as related compositions, kits, and methods.