28915-80-2

Basic information

• Product Name: 2,3,4-tri-O-acetyl-α-L-rhamnopyranose
• Synonyms: 2,3,4-tri-O-acetyl-α-L-rhamnopyranose
• CAS NO: 28915-80-2
• Molecular Weight: 290.27
• Mol File: 28915-80-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,3,4-tri-O-acetyl-α-L-rhamnopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-tri-O-acetyl-α-L-rhamnopyranose(28915-80-2)
• EPA Substance Registry System: 2,3,4-tri-O-acetyl-α-L-rhamnopyranose(28915-80-2)

Safety Data

• Hazardous Substances Data: 28915-80-2(Hazardous Substances Data)

Usage

General Description

2,3,4-tri-O-acetyl-α-L-rhamnopyranose is a chemical compound that belongs to the family of carbohydrates. It is a derivative of α-L-rhamnopyranose, a type of sugar molecule. The compound is characterized by its three acetyl groups, which are attached to the hydroxyl groups of the sugar. This modification of the molecule can impact its solubility, reactivity, and stability. The acetylated form of α-L-rhamnopyranose may be used as a building block in organic synthesis, specifically in the creation of more complex carbohydrates or glycosides. Additionally, this compound may also have potential applications in pharmaceutical research or drug development, due to its ability to interact with specific biological receptors or enzymes. Overall, 2,3,4-tri-O-acetyl-α-L-rhamnopyranose is a valuable chemical with various potential uses in the fields of chemistry and biochemistry.

Upstream product

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

Downstream Products

• 374726-31-5 Acetic acid (3R,4R,5S,6S)-4,5-diacetoxy-2-(bis-benzyloxy-phosphanyloxy)-6-methyl-tetrahydro-pyran-3-yl ester 
• 52628-68-9 2,4-dinitrophenyl-2,3,4-tri-O-acetyl-6-deoxy-β-D-galactopyranoside 
• 1350891-95-0 (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl) 4-nitrophenyl carbonate 
• 167612-34-2 phenyl 6-deoxy-2,3,4-tri-O-acetyl-1-thio-β-L-galactopyranoside 
• 107038-96-0 Phenyl-tri-O-acetyl-1,6-didesoxy-1-thio-β-D-glucopyranosid 

Relevant articles and documents

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.

Structures of new p-hydroxystyrene glycosides, ptelatoside-A and ptelatoside-B isolated from bracken fern, Pteridium aquilinum var. latiusculum, and synthesis of Ptelatoside-A

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