25129-51-5

Basic information

• Product Name: .beta.-D-Arabinofuranoside, methyl
• Synonyms: .beta.-D-Arabinofuranoside, methyl;b-D-Arabinofuranoside, Methyl
• CAS NO: 25129-51-5
• Molecular Formula: C₆H₁₂O₅
• Molecular Weight: 164.16
• Mol File: 25129-51-5.mol
• Article Data: 97

Chemical Properties

• Appearance: /
• CAS DataBase Reference: .beta.-D-Arabinofuranoside, methyl(CAS DataBase Reference)
• NIST Chemistry Reference: .beta.-D-Arabinofuranoside, methyl(25129-51-5)
• EPA Substance Registry System: .beta.-D-Arabinofuranoside, methyl(25129-51-5)

Safety Data

• Hazardous Substances Data: 25129-51-5(Hazardous Substances Data)

Usage

General Description

.beta.-D-Arabinofuranoside, methyl is a chemical compound that belongs to the group of arabinofuranosides. It is a methyl derivative of the sugar molecule D-arabinofuranoside and is commonly used in the field of biochemistry and pharmaceutical research. Methyl arabinofuranoside is known for its ability to penetrate cell membranes and is used as a research tool to study the role of arabinofuranosides in various biological processes. Additionally, it has potential applications in the development of pharmaceuticals and drug delivery systems due to its drug-like properties and ability to interact with biological systems. Overall, methyl arabinofuranoside is a valuable chemical with diverse research and practical applications in the field of biochemistry and pharmaceuticals.

Upstream product

• 67-56-1 methanol 
• 10323-20-3 D-Arabinose 
• 1941-50-0 D-arabinose diethyl dithioacetal 
• 532-20-7 D-arabinofuranose 
• 7647-01-0 hydrogenchloride 
• 56607-40-0 methyl D-arabinofuranoside 
• 1114-34-7 D-lyxose 
• 532-20-7 D-lyxose 
• 87-72-9 D-lyxose 
• 50-69-1 D-ribose 
• 58-86-6 D-xylose 
• 532-20-7 D-xylofuranose 
• 75-36-5 acetyl chloride 
• 609-06-3 L-xylose 

Downstream Products

• 2296-41-5 methyl-tri-O-methyl-arabinofuranoside 
• 79083-40-2 2,3,5-tri-O-benzyl-1-O-methyl-α-D-xylofuranoside 
• 79083-41-3 2,3,5-tri-O-benzyl-1-O-methyl-β-D-xylofuranoside 
• 86042-33-3 methyl 2,3,5-tri-O-p-toluyl-D-ribofuranoside 
• 59279-37-7 methyl 2,3,5-tri-O-(p-nitrobenzoyl)-β-D-ribofuranoside 
• 58763-00-1 ((3aR,4R,6S,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 197716-38-4 2,3,5-tri-O-benzyl-1-O-methyl-D-xylofuranoside 
• 302800-57-3 methyl-2,3,5-tri-O-benzyl-D-lyxofuranoside 
• 303041-42-1 methyl 2,3,5-tri-O-[3-(trifluoromethyl)benzoyl]-D-ribofuranoside 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 532401-38-0 methyl 6-O-trityl-α,β-ribofuranoside 
• 741681-84-5 5-S-acetyl-5-thio-L-arabinofuranoside 
• 148766-45-4 methyl 5-O-trityl-β-D-arabinofuranoside 

Relevant articles and documents

Telescoped Process to Manufacture 6,6,6-Trifluorofucose via Diastereoselective Transfer Hydrogenation: Scalable Access to an Inhibitor of Fucosylation Utilized in Monoclonal Antibody Production

IgG1 monoclonal antibodies with reduced glycan fucosylation have been shown to improve antibody-dependent cellular cytotoxicity (ADCC) by allowing more effective binding of the Fc region of these proteins to T cells receptors. Increased in vivo efficacy in animal models and oncology clinical trials has been associated with the enhanced ADCC provided by these engineered mAbs. 6,6,6-Trifluorofucose (1) is a new inhibitor of fucosylation that has been demonstrated to allow the preparation of IgG1 monoclonal antibodies with lower fucosylation levels and thus improve the ADCC of these proteins. A new process has been developed to support the preparation of 1 on large-scale for wide mAb manufacture applications. The target fucosylation inhibitor (1) was synthesized from readily available d-arabinose in 11% overall yield and >99.5/0.5 dr (diastereomeric ratio). The heavily telescoped process includes seven steps, two crystallizations as purification handles, and no chromatography. The key transformation of the sequence involves the diastereoselective preparation of the desired trifluoromethyl-bearing alcohol in >9/1 dr from a trimethylsilylketal intermediate via a ruthenium-catalyzed tandem ketal hydrolysis-transfer hydrogenation process.

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.