Adenosine 5'-(toluene-4-sulphonate) CAS No. 5135-30-8

Product Description

Adenosine 5'-(toluene-4-sulphonate), also known as adenosine 5'-tosylate or 5′-O-(p-Toluenesulfonyl)adenosine, is a modified nucleoside derivative where the 5'-hydroxyl group of adenosine is esterified with p-toluenesulfonyl chloride (tosyl chloride, TsCl), resulting in the formation of a tosylate (–OTs) group at the 5'-position of adenosine. This compound typically appears as a white to off-white crystalline solid and is soluble in polar organic solvents like DMF and DMSO, though it is poorly soluble in water. The 5'-tosylate group is an excellent leaving group in nucleophilic substitution reactions, allowing it to be displaced by nucleophiles such as halides, amines, and thiols to form 5'-modified adenosine derivatives. It is commonly used in the synthesis of 5'-deoxyadenosine analogs, 5'-thioadenosine derivatives, and other modified nucleosides, acting as an intermediate in the preparation of adenosine-based prodrugs or bioconjugates. Adenosine 5'-tosylate is typically prepared by reacting adenosine with p-toluenesulfonyl chloride in an inert solvent like pyridine or DMF under anhydrous conditions. It finds applications in medicinal chemistry for creating modified nucleosides with potential antiviral or anticancer properties and serves as a precursor for 5'-functionalized adenosine derivatives in biochemical studies. For safety, it should be stored under anhydrous conditions at low temperatures (e.g., -20°C) and handled with care in a fume hood due to its potential toxicity and reactivity.

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Product Use & Characteristics

• Molecular Formula: C₁₇H₁₉N₅O₆S

• Molecular Weight: 421.4 g/mol

• IUPAC Name: [(2R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl 4-methylbenzenesulfonate

• Chemical Name: Adenosine 5'-p-toluenesulfonate

• Abbreviation: Adenosine 5'-OTs (OTs = p-toluenesulfonyloxy)

• Appearance: White to off-white crystalline solid

• Solubility: Soluble in polar organic solvents (e.g., DMF, DMSO); poorly soluble in water

• Stability: More stable in organic solvents compared to free 5'-hydroxyadenosine; suitable for storage and transportation

Synthesis Methods

Adenosine 5'-(toluene-4-sulphonate) is typically synthesized by reacting adenosine with p-toluenesulfonyl chloride (TsCl) in the presence of a base (such as pyridine or triethylamine) in an anhydrous organic solvent (e.g., pyridine, DMF). The base is used to neutralize the HCl generated during the reaction.

Uses

• Organic Synthesis Intermediate: Used as an intermediate in the synthesis of nucleoside analogs, such as precursors of antiviral or anticancer drugs.

• Nucleophilic Substitution Reactions: The 5'-tosylate group (–OTs) is an excellent leaving group, making it useful for alkylating, arylating, or other functional group transformations of the 5' position of adenosine.

• Medicinal Chemistry: Employed in the creation of modified nucleosides with potential antiviral or anticancer properties.

• Biochemical Research: Serves as a precursor for 5'-functionalized adenosine derivatives in biochemical studies.

• Solid Phase Synthesis: Acts as an active intermediate in solid phase synthesis.

• Enzymatic Synthesis: Applied in enzymatic synthesis or for modifying nucleosides for pharmaceutical or molecular biology use.

Safety and Handling

• Storage: Store under anhydrous conditions at low temperatures (e.g., -20°C).

• Handling: Handle with care in a fume hood due to potential toxicity and reactivity.

• Hazards: Irritant; may cause respiratory and skin irritation.

• Storage Conditions: Store in a tightly closed container under dry, cool conditions.

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Sigma Chemical Group is a major chemical enterprise headquartered in Hangzhou, Zhejiang Province, with a diversified portfolio of subsidiaries including Henan Sigma Biotechnology Co., Ltd, QIngdao Sigma Chemical Co.,Ltd, Nanchang Sigma Chemical Co., Ltd., and Jinan Sigma Chemical Co., Ltd. Established on January 16, 2017, Qingdao Sigma Chemical Co., Ltd. operates as a micro-sized chemical product wholesaler with a registered capital of RMB 100,000. Led by legal representative Yang Yuwen and based at 2-1-2301, Jiahe Xinxing, No. 130 Shandong Road, Shibei District, Qingdao, the company’s operations span chemicals, machinery equipment, and import-export services. Henan Sigma Biotechnology Co., Ltd, located in Dongmafang, Muye District, Xinxiang City, Henan Province, specializes in the sales of pesticides, pharmaceuticals, veterinary drugs, and mixed feed additive series, including products like adenine, florfenicol injection, carbasalate calcium soluble powder, and cefotaxime sodium chloride injection. Guided by a win-win and innovative business philosophy, the company employs a modern management approach and customer-centric service, upholding integrity, diligence, and a commitment to quality, thereby earning customer trust through diverse product offerings and competitive pricing. Nanchang Sigma Chemical Co., Ltd., situated in Nanchang, Jiangxi Province, is dedicated to producing high-purity plant extracts, emphasizing eco-friendly, non-toxic chemical raw materials that generate no environmental pollutants. Jinan Sigma Chemical Co., Ltd., located in Jinan, the capital of Shandong Province known as the "City of Springs," focuses on manufacturing active pharmaceutical ingredients (APIs) and pharmaceutical intermediates. The company maintains long-term industry-academia-research collaborations with Shandong University and Qilu University of Technology, continuously enhancing R&D investments to drive innovation and growth.