263709-08-6

Basic information

• Product Name: N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine
• Synonyms: N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine
• CAS NO: 263709-08-6
• Molecular Weight: 675.771
• Mol File: 263709-08-6.mol

Chemical Properties

• CAS DataBase Reference: N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine(CAS DataBase Reference)
• NIST Chemistry Reference: N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine(263709-08-6)
• EPA Substance Registry System: N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine(263709-08-6)

Safety Data

• Hazardous Substances Data: 263709-08-6(Hazardous Substances Data)

Upstream product

• 263709-04-2 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-isocyanato-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 263709-00-8 O-[(tert-butyl)dimethylsilyl]-L-threonine 2-(4-nitrophenyl)ethyl ester 
• 7387-57-7 triacetyladenosine 
• 100-27-6 2-(4-nitrophenyl)ethanol 
• 263709-06-4 N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 2',3',5'-triacetate 

Downstream Products

• 263709-12-2 2'-O-[(tert-butyl)dimethylsilyl]-N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine 
• 263709-10-0 N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine 

Relevant articles and documents

Chemical synthesis of an RNA sequence containing 2-thiocytidine (s 2C): The DY647 labelled anticodon stem and loop sequence of Staphylococcus aureus tRNAArg (s2C32, mnm 5U34, t6A

Incorporation of 2-thiocytidine (s2C) into a DY647 labelled 17-mer RNA sequence corresponding to the anticodon stem loop of Staphylococcus aureus tRNAArg has been achieved by phosphoramidite chemistry. Key to the success was the use

Synthesis of the anticodon hairpin (t)RNA(f)(Met) containing N-{[9-(β- D-ribofuranosyl)-9H-purin-6-yl]carbamoyl}-l-threonine (= N6-{{[(1S,2R)-1- carboxy-2-hydroxypropyl]amino}carbonyl}adenosine, t6A)

As part of our studies on the structure of yeast 1RNA(f)(Met), we investigated the incorporation of N-{[9-(β-D-ribofuranosyl)-9H-purin-6- yl]carbamoyl}-L-threonine (t6A) in the loop of a RNA 17-mer hairpin. The carboxylic function of the L-threonine moiety of t6A was protected with a 2- (4-nitrophenyl)ethyl group, and a (tert-butyl)dimethylsilyl group was used for the protection of its secondary OH group. The 2'-OH function of the standard ribonucleotide building blocks was protected with a [(triisopropylsilyl)oxy]methyl group. Removal of the base-labile protecting groups of the final RNA with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and then with MeNH2 was done under carefully controlled conditions to prevent hydrolysis of the carbamate function, leading to loss of the L-threonine moiety.