51368-20-8

Usage

Uses

Used in Organic Synthesis:
Beta-Xylopyranosyl azide is used as a reagent in organic synthesis for the modification of carbohydrates, which is crucial for studying their biological functions and interactions.
Used in Click Chemistry:
In the field of click chemistry, beta-Xylopyranosyl azide is utilized as a key component to facilitate rapid and efficient chemical reactions, allowing for the formation of complex molecular structures with high selectivity and minimal side effects.
Used in Pharmaceutical Development:
Beta-Xylopyranosyl azide is employed as a building block in the development of glycosylated molecules, which have potential applications in the creation of new pharmaceuticals targeting various diseases.
Used in Materials Science:
In materials science, beta-Xylopyranosyl azide is used for the synthesis of novel glycosylated materials with unique properties, potentially leading to advances in areas such as biocompatibility and drug delivery systems.

Upstream product

• 87-72-9 D-Xylose 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 53784-33-1 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-xylopyranose 

Relevant academic research and scientific papers

One-Pot Stereoselective Synthesis of Glycosyl Azides via 1,2-cyclic Sulfite

In a one-pot procedure, treatment of partially protected or unprotected aldoses with N,N'-thionyldiimidazole and then, lithium azide leads stereoselectively to glycosyl azides.

The search for new amphiphiles: Synthesis of a modular, high-throughput library

Amphiphilic compounds are used in a variety of applications due to their lyotropic liquid-crystalline phase formation, however only a limited number of compounds, in a potentially limitless field, are currently in use. A library of organic amphiphilic compounds was synthesised consisting of glucose, galactose, lactose, xylose and mannose head groups and double and triple-chain hydrophobic tails. A modular, high-throughput approach was developed, whereby head and tail components were conjugated using the coppercatalysed azide-alkyne cycloaddition (CuAAC) reaction. The tails were synthesised from two core alkyne-tethered intermediates, which were subsequently functionalised with hydrocarbon chains varying in length and degree of unsaturation and branching, while the five sugar head groups were selected with ranging substitution patterns and anomeric linkages. A library of 80 amphiphiles was subsequently produced, using a 24-vial array, with the majority formed in very good to excellent yields. A preliminary assessment of the liquid-crystalline phase behaviour is also presented