42776-78-3

Basic information

• Product Name: 2'-TOSYLADENOSINE
• Synonyms: 2'-TOSYLADENOSINE;2′-O-p-Toluenesulfonyladenosine
• CAS NO: 42776-78-3
• Molecular Formula: C₁₇H₁₉N₅O₆S
• Molecular Weight: 421.42766
• Mol File: 42776-78-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 222-223 °C
• Boiling Point: 772.1±70.0 °C(Predicted)
• Appearance: /
• Density: 1.75±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C
• PKA: 12.61±0.70(Predicted)
• CAS DataBase Reference: 2'-TOSYLADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-TOSYLADENOSINE(42776-78-3)
• EPA Substance Registry System: 2'-TOSYLADENOSINE(42776-78-3)

Safety Data

• Hazardous Substances Data: 42776-78-3(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 58-61-7 adenosine 
• 42822-80-0 2',3'-O-(dibutylstannylene)adenosine 
• 6554-24-1 3',5'-di-O-acetyladenosine 
• 2140-25-2 5'-O-acetyladenosine 
• 7473-45-2 1-O-methyl-D-ribofuranose 
• 103292-04-2 3,5-di-O-(p-toluoyl)-2-O-(p-toluolsulfonyl)-β-D-methyl ribofuranoside 
• 103292-02-0 Toluene-4-sulfonic acid (2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-2-methoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester 
• 76700-76-0 (6aR,8R,9R,9aS)-2,2,4,4-tetraisopropyl-8-methoxytetrahydro-6H-furo[3,2- f][1,3,5,2,4]trioxadisilocin-9-ol 
• 532-20-7 D-Ribose 
• 4546-55-8 N-benzoyladenosine 
• 69304-45-6 3',5'-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)adenosine 
• 103292-06-4 3',5'-di-O-toluoyl 2'-tosyl adenosine 
• 103292-03-1 Toluene-4-sulfonic acid (2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-2-methoxy-tetrahydro-furan-3-yl ester 

Downstream Products

• 117654-61-2 9-(3'-C-methyl-5'-O-(triphenylmethyl)-2'-deoxy-β-D-xylofuranosyl)adenine 
• 958-09-8 2'-deoxy-D-adenosine 
• 87422-40-0 9-(2-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)adenine 
• 124040-43-3 N⁶,O⁵'-bis(4,4'-dimethoxytrityl)-3'-O-mesyladenosine 
• 124040-46-6 N⁶-(4,4'-dimethoxytrityl)-9-(2-deoxy-3-O-mesyl-5-O-trityl-β-D-threo-pentofuranosyl)adenine 
• 124040-45-5 N⁶-(4,4'-dimethoxytrityl)-9-(2-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)adenine 
• 124040-47-7 9-(2-deoxy-3-O-mesyl-5-O-trityl-β-D-threo-pentofuranosyl)adenine 
• 66503-50-2 9-<(3S)-azido-2,3-dideoxy-5-O-trityl-β-D-glycero-pentofuranosyl>adenine 
• 114743-29-2 N⁶,O^5'-bis(4,4'-dimethoxytrityl)-9-(3-deoxy-2-O-mesyl-β-D-threo-pentofuranosyl)adenine 
• 114743-30-5 N⁶,O^5'-bis(4,4'-dimethoxytrityl)-9-<(2R)-2-azido-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine 
• 114743-31-6 N⁶,O⁵'-bis(4,4'-dimethoxytrityl)-9-(3-deoxy-β-D-threo-pentofuranosyl)adenine 
• 184297-07-2 Toluene-4-sulfonic acid (2R,3R,4R,5R)-2-(6-amino-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-phenoxythiocarbonyloxy-tetrahydro-furan-3-yl ester 
• 184297-12-9 Toluene-4-sulfonic acid (2R,3R,5S)-2-(6-amino-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester 
• 190773-84-3 9-[3-deoxy-3-fluoro-2,5-di-O-(p-toluenesulfonyl)-β-D-xylopyranosyl]adenine 

Relevant articles and documents

An effective and convenient synthesis of cordycepin from adenosine

Cordycepin is a purine nucleoside analog with potent and diverse biological activities. Herein, we designed two methods to synthesize cordycepin. One method mainly converted the 3′-OH group into an iodide group and further dehalogenation to yield the final product. Although this method presented a short synthetic procedure, the synthesis had a low overall yield, resulting in only 13.5% overall yield. To improve the overall yield of cordycepin, another synthetic route was studied, which consisted of four individual steps: (1) 5′-OH protection (2) esterification (3) -O-tosyl (-OTs) group removal (4) deprotection. The key step in the synthetic method involved the conversion of 5′-O-triphenylmethyladenosine to 3′-O-tosyl-5′-O-triphenylmethyladenosine, using LiAlH4 as reducing agent. The main advantages of this route were an acceptable total product yield and the commercial availability of all starting materials. The optimal reaction conditions for each step of the route were identified. The overall yield of cordycepin obtained from adenosine as the starting material was 36%.

Deoxygenative [1,2]-hydride shift rearrangements in nucleoside and sugar chemistry: Analogy with the [1,2]-electron shift in the deoxygenation of ribonucleotides by ribonucleotide reductases

(Chemical Equation Presented) A variant of the semipinacol rearrangement that was observed in our laboratory has been applied to the synthesis of several furanose and pyranose derivatives. The process consists of an "orchestrated" [1,2]-hydride shift with

One-pot p-toluenesulfonylation of adenosine and methyl glycosides with a substoichiometric amount of organotin mediators

A substoichiometric amount (10-20 mol%) of dibutyltin dichloride 1 was found to be effective for promoting the regioselective 2′-O-tosylation of adenosine 2 with TsCl in a one-pot manner, wherein a turnover step for tin dichloride 1 was involved. Dibutylc