211919-88-9

Basic information

• Product Name: (5?'S)-N⁶-benzoyl-3?'-O-(tert-butyldimethylsilyl)-5?',8-cyclo-2?'-deoxyadenosine
• Synonyms: (5?'S)-N⁶-benzoyl-3?'-O-(tert-butyldimethylsilyl)-5?',8-cyclo-2?'-deoxyadenosine
• CAS NO: 211919-88-9
• Molecular Weight: 467.6
• Mol File: 211919-88-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (5?'S)-N⁶-benzoyl-3?'-O-(tert-butyldimethylsilyl)-5?',8-cyclo-2?'-deoxyadenosine(CAS DataBase Reference)
• NIST Chemistry Reference: (5?'S)-N⁶-benzoyl-3?'-O-(tert-butyldimethylsilyl)-5?',8-cyclo-2?'-deoxyadenosine(211919-88-9)
• EPA Substance Registry System: (5?'S)-N⁶-benzoyl-3?'-O-(tert-butyldimethylsilyl)-5?',8-cyclo-2?'-deoxyadenosine(211919-88-9)

Safety Data

• Hazardous Substances Data: 211919-88-9(Hazardous Substances Data)

Upstream product

• 35824-20-5 N-benzoyl-5-tosyl-2'-deoxyadenosine 
• 211919-84-5 N-[9-((2R,4S,5S)-4-Hydroxy-5-phenylsulfanylmethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide 
• 211919-86-7 N⁵-benzoyl-3'-O-(tert-butyldimethylsilyl)-5',8-cyclo-2',5-dideoxyadenosine 
• 211919-85-6 N⁶-benzoyl-5',8-cyclo-2',5'-dideoxyadenosine 
• 4546-72-9 N₆-benzoyl-2'-deoxyadenosine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 51549-40-7 6-N-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine 
• 167700-45-0 5'-aldehyde-2'-deoxy-6-N-benzoyl-3'-O-tertbutyldimethylsilyl adenosine 
• 898253-81-1 (5'S,8R)-N-benzoyl-O₃'-(tert-butyldimethylsilyl)-5',8-cyclo-7,8-dihydro-2'-deoxyadenosine 
• 872131-62-9 (5'S)-N⁵-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-[tris(trimethylsilyl)silyl]-5',8-cyclo-2'-deoxyadenosine 
• 211919-87-8 N⁶-benzoyl-3'-O-(tert-butyldimethylsilyl)-5',8-cyclo-5'-oxo-2'-deoxyadenosine 

Downstream Products

• 222736-09-6 (5'R)-N₆-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4-dimethoxytrityl)-5',8-cyclo-2'-deoxyadenosine 
• 222736-10-9 (5'R)-N₆-benzoyl-5'-O-(4,4-dimethoxytrityl)-5',8-cyclo-2'-deoxyadenosine 
• 222736-08-5 (5?'R)-N⁶-benzoyl-3?'-O-(tert-butyldimethylsilyl)-5?',8-cyclo-2?'-deoxyadenosine 
• 222736-07-4 C₂₄H₃₁N₅O₆SSi 

Relevant articles and documents

C5′-adenosinyl radical cyclization. A stereochemical investigation

A variety of substituted 2′-deoxyadenosin-5′-yl radicals 3 were generated under different reaction conditions. Radicals 3 underwent intramolecular cyclization onto the C8-N7 double bond of the adenine moiety leading to aminyl radicals (5′S,8R)-4 and (5′R,8R)-4 and, eventually, to the corresponding cyclonucleosides 5 and 6. The effect of the solvent, the nature of the substituents, and the generation method of radicals 3 on the stereoselectivity of the C5′-radical cyclization have been considered. The observed increase of the (5′S)/(5′R) ratio by increasing the bulkiness of the R1 group is explained in terms of steric repulsion between R1 and the purine moiety which favors the C5′-endo conformation, whereas the effect of the water solvent in promoting the (5′R)-stereoselective cyclization is ascribed to intermolecular hydrogen bonding stabilizing the C5′-exo confomation.

Site-Specific Introduction of (5'S)-5',8-Cyclo-2'-deoxyadenosine into Oligodeoxyribonucleotides

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