202824-32-6

Basic information

• Product Name: Phenyl 3,4-O-(2,3-Dimethoxybutan-2,3-diyl)-1-thio-α-L-rhamnopyranoside
• Synonyms: Phenyl 3,4-O-(2,3-Dimethoxybutan-2,3-diyl)-1-thio-α-L-rhamnopyranoside;Phenyl 6-deoxy-3,4-O-[(1R,2R)-1,2-diMethoxy-1,2-diMethyl-1,2-ethanediyl]-1-thio-α-L-Mannopyranoside
• CAS NO: 202824-32-6
• Molecular Formula: C₁₈H₂₆O₆S
• Molecular Weight: 370.46044
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives;Sulfur & Selenium Compounds
• Mol File: 202824-32-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: Phenyl 3,4-O-(2,3-Dimethoxybutan-2,3-diyl)-1-thio-α-L-rhamnopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl 3,4-O-(2,3-Dimethoxybutan-2,3-diyl)-1-thio-α-L-rhamnopyranoside(202824-32-6)
• EPA Substance Registry System: Phenyl 3,4-O-(2,3-Dimethoxybutan-2,3-diyl)-1-thio-α-L-rhamnopyranoside(202824-32-6)

Safety Data

• Hazardous Substances Data: 202824-32-6(Hazardous Substances Data)

Usage

Description

Phenyl 3,4-O-(2,3-Dimethoxybutan-2,3-diyl)-1-thio-α-L-rhamnopyranoside is a complex organic compound characterized by its unique chemical structure, which includes a phenyl group, a thio-linkage, and a rhamnopyranoside moiety. It is an oily substance with potential applications in various fields due to its chemical properties.

Uses

Used in Organic Synthesis:
Phenyl 3,4-O-(2,3-Dimethoxybutan-2,3-diyl)-1-thio-α-L-rhamnopyranoside is used as a key intermediate in organic synthesis for the development of new compounds with specific properties and applications. Its unique structure allows for various chemical reactions and modifications, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Phenyl 3,4-O-(2,3-Dimethoxybutan-2,3-diyl)-1-thio-α-L-rhamnopyranoside is used as a precursor for the synthesis of bioactive molecules with potential therapeutic applications. Its ability to form stable linkages with other molecules makes it a promising candidate for the development of new drugs and drug delivery systems.
Used in Agrochemical Industry:
Phenyl 3,4-O-(2,3-Dimethoxybutan-2,3-diyl)-1-thio-α-L-rhamnopyranoside is also utilized in the agrochemical industry for the synthesis of novel pesticides, herbicides, and other crop protection agents. Its unique chemical properties enable the development of more effective and environmentally friendly agrochemicals.
Used in Specialty Chemicals:
In the specialty chemicals sector, Phenyl 3,4-O-(2,3-Dimethoxybutan-2,3-diyl)-1-thio-α-L-rhamnopyranoside is employed as a component in the synthesis of various specialty chemicals, such as dyes, fragrances, and functional materials. Its versatility and reactivity contribute to the creation of innovative products with specific properties and applications.

Upstream product

• 1214-98-8 phenyl 1-thio-α-L-rhamnopyranose 
• 176798-33-7 2,2,3,3-tetramethoxybutane 
• 431-03-8 dimethylglyoxal 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 709619-84-1 phenyl 2-O-acetyl-(2'R,3'R)-3,4-O-2',3'-dimethoxybutane-2',3'-diyl-1-thio-α-L-rhamnopyranoside 
• 1619930-78-7 C₁₃H₁₈O₄S 
• 1619930-79-8 C₂₅H₄₆O₄SSi₂ 
• 1619930-80-1 C₂₅H₄₆O₅SSi₂ 
• 202824-35-9 C₆₇H₉₂O₁₆ 
• 202824-36-0 (R)-3-{(R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxydecanoic acid 
• 202824-33-7 (R)-3-[(2R,3R,4aS,5S,7R,8R,8aR)-2,3-Dimethoxy-2,3,5-trimethyl-8-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,4-b][1,4]dioxin-7-yloxy]-decanoic acid 2-oxo-2-phenyl-ethyl ester 
• 202824-37-1 (R)-3-{(R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxy-(R)-decanoic acid 
• 1055030-00-6 (R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-L-rhamnopyranosyl]oxydecanoic acid 
• 125135-03-7 rhamnolipid 
• 849938-12-1 phenyl 2-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-α-L-rhamnopyranoside 
• 709619-81-8 phenyl 2-O-methyl-(2'R,3'R)-3,4-O-2',3'-dimethoxybutane-2',3'-diyl-1-thio-α-L-rhamnopyranoside 

Relevant articles and documents

Total synthesis and stereochemical reassignment of mandelalide A

The total synthesis of the tunicate metabolite mandelalide A and the correction of its originally assigned stereochemistry are reported. Key features of the convergent, fully stereocontrolled route include the use of a Prins cyclization for the diastereoselective construction of the tetrahydropyran subunit, Rychnovsky-Bartlett cyclization for the preparation of the tetrahydrofuran moiety, Suzuki coupling, Horner-Wadsworth-Emmons macrocyclization, and glycosylation to append the L-rhamnose-derived pyranoside.

Synthesis of a potent and selective inhibitor of p90 Rsk

(Chemical Equation Presented) The synthesis of the naturally occurring kaempferol glycoside SL0101 has been accomplished, as has its biochemical evaluation. SL0101 exhibits selective and potent p90 Rsk inhibitory activity at nanomolar concentrations without inhibiting the function of upstream kinases such as MEK, Raf, or PKC. The synthesis verified the structural assignment of the natural product and has provided access to material sufficient for detailed biological evaluation.

An efficient synthesis of (R)-3-{(R)-3-[2-O-(α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl] oxydecanoyl}oxydecanoic acid, a rhamnolipid from Pseudomonas aeruginosa

N-iodosuccinmide/triflic acid mediated one-pot two-step glycosylation of ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamnopyranoside (8) with phenyl 3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-α-L-rhamnopyranoside (10b) and phenacyl (R)-3-hydroxydecanoate (13) gave rhainnolipid 17. The latter was transformed in five steps into the title compound 2. Esterification of 2 with diazomethane resulted into the corresponding methyl ester derivative 1.