131087-35-9

Usage

Uses

Used in Organic Chemistry:
Phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside is used as a substrate in enzymatic reactions for its ability to facilitate the transfer of the rhamnose moiety to an acceptor molecule, which is crucial in the synthesis of various glycoside-based compounds.
Used in Biochemical Research:
In biochemical research, phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside is employed as a building block for the synthesis of complex carbohydrates and glycoconjugates, which are essential for studying the biological roles of carbohydrates and their interactions with proteins and other biomolecules.
Used in Pharmaceutical Industry:
Phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside is used as a key intermediate in the development of pharmaceuticals, particularly in the synthesis of glycosylated drug molecules that can improve the pharmacokinetic and pharmacodynamic properties of drugs.
Used in Material Science:
In material science, phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside can be used as a component in the design of new materials with specific properties, such as self-assembling systems or stimuli-responsive materials, by exploiting its ability to form glycosidic linkages.
Used in Analytical Chemistry:
Phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside is utilized as a reference compound in the development and validation of analytical methods for the detection and quantification of carbohydrates and their derivatives in various samples, including biological fluids and complex mixtures.

Upstream product

• 1214-98-8 phenyl 1-thio-α-L-rhamnopyranose 
• 67-64-1 acetone 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 108-98-5 thiophenol 
• 73-34-7 L-rhamnose 
• 883884-80-8 1,2,3,4-tetra-O-acetyl-L-rhamnose 
• 6014-42-2 L-rhamnose 
• 108740-74-5 phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 331456-83-8 S-phenyl 2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside 
• 940006-60-0 phenyl 2,3-O-isopropylidene-4-O-(2-naphthylmethyl)-1-thio-α-L-rhamnopyranoside 
• 145836-07-3 phenyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside 
• 327603-72-5 phenyl 3-O-(methylthio)carbonyl-4-O-methyl-2-S-phenyl-2,6-di-deoxy-β-L-glucopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 
• 153693-37-9 phenyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 
• 172296-66-1 Phenyl 3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 
• 636559-71-2 phenyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

l-Rhamnosylation: The Solvent is the Solution

Herein we present a systematic study of l-rhamnosylation. The influence of protective groups, reactivity, solvents and glycosylation method, i.e. catalytic versus promoted glycosylation, are studied. It was found that the selectivity can be controlled to

A Novel Cleavage of Allyl Protection

A novel, efficient, and mild cleavage of allyl protection is developed employing perfluoroalkylation and subsequent elimination.

A concise synthesis of rhamnan oligosaccharides with alternating α-(1→2)/(1→3)-linkages and repeating α-(1→3)-linkages by iterative α-glycosylation using disaccharide building blocks

A concise synthetic route to rhamnan oligosaccharides with alternating α-(1→2)/(1→3)-linkages and repeating α-(1→3)-linkages is reported. This synthesis was achieved by iterative α-glycosylation using disaccharide building blocks and through orthogonal co

Efficient synthesis of O-antigen fragments expressed by Burkholderia anthina by modular synthesis approach

To facilitate mapping of the interaction region of the O-chain of the lipopolysaccharide from Burkholderia anthina and of a lipopolysaccharide-specific monoclonal antibody, trisaccharide propyl α-l-rhamnopyranosyl-(1→2)-α-d-galactopyranosyl-(1→3)-α-l-rham

Synthesis of all eight stereoisomeric 6-deoxy-l-hexopyranosyl donors - Trends in using stereoselective reductions or mitsunobu epimerizations

The synthesis of all eight rare but biologically important 6deoxy-L-hexoses as their thioglycoside glycosyl donors starting from the commercially available L-rhamnose or L-fucose is reported. The synthesis of all eight 6-deoxy-L-hexoses was accomplished u

RSK INHIBITORS AND THERAPEUTIC USES THEREOF

The present invention is directed to novel compounds and compositions that have Rsk specific inhibitory activity. In addition, inhibition of Rsk by the present compounds has been discovered to halt the proliferation of cancer cell lines while having little effect on the proliferation rate of normal cells. Therefore, the present invention identifies Rsk as a target for therapeutic intervention in diseased states in which the disease or the symptoms can be ameliorated by inhibition of Rsk catalytic activity.

Synthesis of the Salmonella type E(1) core trisaccharide as a probe for the generality of 1-(benzenesulfinyl)piperidine/triflic anhydride combination for glycosidic bond formation from thioglycosides.

A synthesis of a chromogenic glycoside of the Salmonella anatum group E(1) core trisaccharide is presented in which all three glycosidic bonds, a 1,2-cis-equatorial, a 1,2-trans-axial, and a 1,2-trans-equatorial linkage representing three of the four main classes of glycosidic bond, are formed with thioglycoside donors activated under a single set of conditions by the combination of 1-(benzenesulfinyl)piperidine and trifluoromethanesulfonic anhydride. 2,3-O-Carbonyl- and 2,3-O-isopropylidene-alpha-L-rhamnopyranosyl thioglycosides are found to be highly alpha-selective rhamnosyl donors under these conditions.

Stereoselective synthesis of 2-S-ethyl(phenyl)-2-thio-β-glucopyranosides via 1,2-migration and concurrent glycosidation of ethyl(phenyl) 2,3-orthoester-1-thio-α-mannopyranosides

1,2-Migration and concurrent glycosidation of ethyl(phenyl) 2,3-orthoester-1-thio-α-D- and L-mannopyranosides under the action of TMSOTf readily afforded the corresponding 2-S-ethyl(phenyl)-2-thio-β-glucopyranosides, ready precursors to 2-deoxy-arabino-hexopyranosides (2-deoxy-β-glucopyranosides).

A new strategy in oligosaccharide synthesis using lipophilic protecting groups: synthesis of a tetracosasaccharide

The use of lipophilic, acyl-type protecting groups in the synthesis of higher-membered oligosaccharides is described by the example of oligosaccharides corresponding to the O-specific polysaccharide (O-SP) of Shigella dysenteriae type 1. Thus, O-stearoyla

A novel and expeditious approach to the stereoselective synthesis of 2- S-ethyl(phenyl)-2-deoxy-β-glycosides, ready precursors to 2-deoxy-β- glycosides

1,2-Migration and concurrent glycosidation of ethyl(phenyl) 2,3- orthoester-1-thio-α-L-rhamnopyranosides under the action of TMSOTf readily afforded the corresponding 2-S-ethyl(phenyl)-2-deoxy-β-glycosides, ready precursors to 2-deoxy-β-glycosides. (C) 2000 Elsevier Science Ltd.