75532-26-2

Basic information

• Product Name: C₁₀H₈O₄S
• Synonyms: C₁₀H₈O₄S
• CAS NO: 75532-26-2
• Molecular Weight: 224.237
• Mol File: 75532-26-2.mol

Chemical Properties

• CAS DataBase Reference: C₁₀H₈O₄S(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₀H₈O₄S(75532-26-2)
• EPA Substance Registry System: C₁₀H₈O₄S(75532-26-2)

Safety Data

• Hazardous Substances Data: 75532-26-2(Hazardous Substances Data)

Upstream product

• 110-00-9 furan 
• 75532-25-1 2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride 

Downstream Products

• 110-00-9 furan 
• 75532-25-1 2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride 
• 56-25-7 cantharidin 

Relevant articles and documents

The novel method to synthesis of cantharidin intermediate

Sulfur-containing dehydrocantharidin(SD) was yielded (76% to 96%) by Diels-Alder reaction in an ionic-liquid system under ordinary pressure and temperature. We explored the influences of different ionic-liquid types, reaction temperatures, and reaction times in this reaction. We found that the optimal reaction temperature was about 35°C, the reaction time was 20 h, and the most suitable ionic liquid was 1-butyl-3-methylimidazolium tetrafluoroborate. Furthermore, in the recycling process of ionic liquid, we found that CH3CN was the most suitable extraction solvent. We explored four steps in the synthetic route to SD and achieved a good yield of 38% in total. We envisage that this process could be further developed at an industrial scale for the synthesis of Cantharidin and is destined to be an environmentally friendly way to solve the lack of cantharis as a natural resource.

SYNTHESIS OF CANTHARIDIN

The invention provides synthetic methods for the preparation of cantharidin and analogs thereof. In one aspect, the invention provides an improved Diels-Alder cycloaddition to generate a key intermediate en route to cantharidin and analogs thereof. In certain embodiments, the new Diels-Alder reaction involves reacting Compound (2) in the presence of furan, and in the absence of acid or increased pressure, in an aprotic polar solvent with slight warming, to yield Compound (1) in favorable yield and exo-endo ratio. In another aspect, the invention also provides a new Diels-Alder reaction between compounds of Formula (III) and furan to yield compounds of Formula (IV), which can then be transformed into cantharidin or analogs thereof. In yet another aspect, the invention describes a new palladium-mediated carbonylation providing another key intermediate en route to cantharidin and analogs thereof. In addition to synthetic methods, present invention also provides compounds {i.e., intermediates) useful in the synthesis of cantharidin and analogs thereof. Compounds provided herein may have biological activity, and therefore may be used in the treatment of diseases or conditions {e.g., infectious diseases and skin conditions).

COMMERCIALLY VIABLE SYNTHESIS OF CANTHARIDIN AND BIOACTIVE CANTHARIDIN DERIVATIVES

The present disclosure provides methods for synthesizing cantharidin and cantharidin derivatives.

Compositions and methods for the protection of nucleophilic groups

The present invention provides compositions, methods, and kits relating to the protection and deprotection of molecules comprising nucleophilic groups, such as the protection and deprotection of thermostable polymerases. Also provided are methods of performing nucleic acid amplification using polymerases protected according to the invention.