28915-80-2

Usage

Uses

Used in Organic Synthesis:
2,3,4-tri-O-acetyl-α-L-rhamnopyranose is used as a building block for the creation of more complex carbohydrates or glycosides. Its acetylated structure allows for further chemical modifications, making it a valuable intermediate in the synthesis of various organic compounds.
Used in Pharmaceutical Research:
2,3,4-tri-O-acetyl-α-L-rhamnopyranose is used as a potential candidate in pharmaceutical research due to its ability to interact with specific biological receptors or enzymes. Its unique chemical properties may contribute to the development of new drugs or therapeutic agents, particularly in the context of carbohydrate-based drug design.
Used in Drug Development:
2,3,4-tri-O-acetyl-α-L-rhamnopyranose is used as a component in drug development, where its interactions with biological targets can lead to the discovery of novel therapeutic agents. Its potential applications in this field highlight the importance of understanding the structure-activity relationships of carbohydrate derivatives in the context of medicinal chemistry.

Upstream product

• 108-24-7 acetic anhydride 
• 90852-99-6 ptelatoside-B 
• 1403377-44-5 C₂₇H₂₆O₇S 
• 113893-72-4 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 
• 122089-71-8 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 

Downstream Products

• 144174-65-2 Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-2-[(2S,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-tetrahydro-pyran-4-yloxy]-6-methyl-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Investigation on the Synthesis of Shigella flexneri Specific Oligosaccharides Using Disaccharides as Potential Transglucosylase Acceptor Substrates

Chemo-enzymatic strategies hold great potential for the development of stereo- and regioselective syntheses of structurally defined bioactive oligosaccharides. Herein, we illustrate the potential of the appropriate combination of a planned chemo-enzymatic pathway and an engineered biocatalyst for the multistep synthesis of an important decasaccharide for vaccine development. We report the stepwise investigation, which led to an efficient chemical conversion of allyl α-d-glucopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→3)-2-deoxy-2-trichloroacetamido-β-d-glucopyranoside, the product of site-specific enzymatic α-d-glucosylation of a lightly protected non-natural disaccharide acceptor, into a pentasaccharide building block suitable for chain elongation at both ends. Successful differentiation between hydroxyl groups features the selective acylation of primary alcohols and acetalation of a cis-vicinal diol, followed by a controlled per-O-benzylation step. Moreover, we describe the successful use of the pentasaccharide intermediate in the [5 + 5] synthesis of an aminoethyl aglycon-equipped decasaccharide, corresponding to a dimer of the basic repeating unit from the O-specific polysaccharide of Shigella flexneri 2a, a major cause of bacillary dysentery. Four analogues of the disaccharide acceptor were synthesized and evaluated to reach a larger repertoire of O-glucosylation patterns encountered among S. flexneri type-specific polysaccharides. New insights on the potential and limitations of planned chemo-enzymatic pathways in oligosaccharide synthesis are provided.

Convergent synthesis and cytotoxic activities of 26-thio- and selenodioscin

Convergent block syntheses of 26-thio- and selenodioscin have been achieved by developing the highly stereoselective 1,2-trans glycosylations of chacotriosyl imidate without recourse to neighboring group assistance. Both thiodioscin and selenodioscin possess cytotoxic activities similar to dioscin, a natural spirostanol glycoside.