131724-82-8

Basic information

• Product Name: Phenyl 1-Thio-α-L-rhamnopyranoside
• Synonyms: Phenyl 1-Thio-α-L-rhamnopyranoside;Phenyl 6-Deoxy-1-thio-α-L-Mannopyranoside
• CAS NO: 131724-82-8
• Molecular Formula: C₁₂H₁₆O₄S
• Molecular Weight: 256.31804
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives;Sulfur & Selenium Compounds
• Mol File: 131724-82-8.mol

Chemical Properties

• Melting Point: 98°C
• Appearance: /
• Solubility: DMF, Methanol
• CAS DataBase Reference: Phenyl 1-Thio-α-L-rhamnopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl 1-Thio-α-L-rhamnopyranoside(131724-82-8)
• EPA Substance Registry System: Phenyl 1-Thio-α-L-rhamnopyranoside(131724-82-8)

Safety Data

• Hazardous Substances Data: 131724-82-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Phenyl 1-Thio-α-L-rhamnopyranoside is used as a synthetic building block for the development of complex organic molecules. Its unique structure allows it to be a valuable component in the synthesis of a wide range of organic compounds, contributing to the advancement of chemical research and the creation of novel materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Phenyl 1-Thio-α-L-rhamnopyranoside is used as a key intermediate in the synthesis of various drugs and pharmaceutical agents. Its ability to be incorporated into complex molecular structures makes it a valuable asset in the development of new medications and therapies.
Used in Chemical Research:
Phenyl 1-Thio-α-L-rhamnopyranoside is also utilized in chemical research as a tool to study the properties and reactions of different organic compounds. Its unique structure allows researchers to gain insights into the behavior of various molecules and contributes to the broader understanding of organic chemistry.

Upstream product

• 108740-74-5 phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 
• 3615-41-6 L-Rhamnose 
• 108-98-5 thiophenol 
• 940006-58-6 S-phenyl 2-O-acetyl-4-O-benzyl-3-O-(4-methoxybenzyl)-α-L-thiorhamnopyranoside 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 73-34-7 L-rhamnose 
• 30021-94-4 1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 
• 6014-42-2 L-rhamnose 
• 883884-80-8 1,2,3,4-tetra-O-acetyl-L-rhamnose 
• 153745-67-6 phenyl 2,3,4-tri-O-acetyl-1-thio-β-L-rhamnopyranoside 

Downstream Products

• 137016-95-6 phenyl 2,3-O-fluoren-9-ylidene-1-thio-α-L-rhamnopyranoside 
• 131087-35-9 phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 
• 131675-54-2 phenyl 3-O-methyl-1-thio-α-L-rhamnopyranoside 
• 172276-94-7 phenyl 4-O-acetyl-1-thio-α-L-rhamnopyranoside 
• 202824-32-6 phenyl (2'R,3'R)-3,4-O-2',3'-dimethoxybutane-2',3'-diyl-1-thio-α-L-rhamnopyranoside 
• 403646-43-5 S-phenyl 2,3-O-carbonyl-1-thio-α-L-rhamnopyranoside 
• 108740-74-5 phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 
• 940006-51-9 S-phenyl 3-O-(2-naphthylmethyl)-α-L-thiorhamnopyranoside 
• 940006-52-0 S-phenyl 3-O-benzyl-α-L-thiorhamnopyranoside 
• 230948-99-9 C₂₀H₂₂O₅S 
• 947256-89-5 phenyl 6-deoxy-2,3,4-tri-O-tert-butyldimethylsilyl-1-thio-α-L-mannopyranoside 
• 849938-16-5 phenyl 2-O-benzyl-1-thio-α-L-rhamnopyranoside 
• 940006-62-2 phenyl 2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 
• 940006-53-1 S-phenyl 2,4-di-O-benzyl-3-O-(2-naphthylmethyl)-α-L-thiorhamnopyranoside 

Relevant articles and documents

Slow glycosylation: Activation of trichloroacetimidates under mild conditions using lithium salts and the role of counterions

Glycosylations were carried out with the two glycosyl donors 4-O-acetyl-2,3-O-isopropylidene-1-O-trichloroacetimidoyl-α-L-rhamnopyranose and 2,3,4-tri-O-benzyl-1-O-trichloro-acetimidoyl-α-L-rhamnopyranose in combination with the two alcohols 1-adamantanol and L-menthol as model glycosyl acceptors. As catalysts, the five lithium salts LiNTf2, LiI, LiClO4, LiPF6 and LiOTf were investigated. We demonstrated that both lithium and the respective counterions are playing a role in the activation of trichloroacetimidate glycosyl donors at rt. Under these very mild conditions, the glycosylations are slow and completed in two to eight days. Depending on the counterion, the rate and yield of the reaction differs; however, the selectivity of all investigated lithium salts is deficient.

Synthesis of Cardiotonic Steroids Oleandrigenin and Rhodexin B

This article describes a concise synthesis of cardiotonic steroids oleandrigenin (7) and its subsequent elaboration into the natural product rhodexin B (2) from the readily available intermediate (8) that could be derived from the commercially available steroids testosterone or DHEA via three-step sequences. These studies feature an expedient installation of the β16-oxidation based on β14-hydroxyl-directed epoxidation and subsequent epoxide rearrangement. The following singlet oxygen oxidation of the C17 furan moiety provides access to oleandrigenin (7) in 12 steps (LLS) and a 3.1% overall yield from 8. The synthetic oleandrigenin (7) was successfully glycosylated with l-rhamnopyranoside-based donor 28 using a Pd(II)-catalyst, and the subsequent deprotection under acidic conditions provided cytotoxic natural product rhodexin B (2) in a 66% yield (two steps).

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

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

Using biological performance similarity to inform disaccharide library design

Designing better small-molecule discovery libraries requires having methods to assess the consequences of different synthesis decisions on the biological performance of resulting library members. Since we are particularly interested in how stereochemistry

Facile oxidative cleavage of 4-O-benzyl ethers with dichlorodicyanoquinone in rhamno- and mannopyranosides

On exposure to dichlorodicyanoquinone in wet dichloromethane at room temperature, equatorial 4-O-benzyl ethers are removed with moderate selectivity in the presence of other benzyl ethers in glycopyranosides and glycothiopyranosides.

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.

Conformational analysis of sulfur-containing 6-deoxy-L-hexose derivatives by molecular modeling and NMR spectroscopy. A theoretical study and experimental evidence of intramolecular nonbonded interactions between sulfur and oxygen

6-Deoxy-L-mannose diphenyldithioacetal (1) unexpectedly gave the rearranged products phenyl 3,4-di-O-acetyl-2-S-phenyl-1,2-dithio-6-deoxy-β -L-glucopyranoside (9) and 3,4-di-O-acetyl-2,5-anhydro-6-deoxy-L-glucose diphenyldithioacetal (10) upon treatment w

Total synthesis of calonyctin A2, a macrolidic glycolipid with plant growth-promoting activity

Calonyctin A2, a tetrasaccharidic glycolipid having a 22-membered macrolidic structure, has been synthesized by the assembly of three 6- deoxygenated thioglycoside intermediates. The short-step synthesis was achieved by preparation of the most complicated