121076-16-2

Basic information

• Product Name: 5'-O-(4,4'-DiMethoxytrityl)-N6-Phenoxyacetyl adenosine
• Synonyms: 5'-O-(4,4'-DiMethoxytrityl)-N6-Phenoxyacetyl adenosine;5'-O-[bis(4-Methoxyphenyl)phenylMethyl]-N6-(2-phenoxyacetyl)adenosine;5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-N-(phenoxyacetyl)adenosine
• CAS NO: 121076-16-2
• Molecular Formula: C₃₉H₃₇N₅O₈
• Molecular Weight: 703.73978
• Mol File: 121076-16-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.36±0.1 g/cm3(Predicted)
• PKA: 7.87±0.43(Predicted)
• CAS DataBase Reference: 5'-O-(4,4'-DiMethoxytrityl)-N6-Phenoxyacetyl adenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4,4'-DiMethoxytrityl)-N6-Phenoxyacetyl adenosine(121076-16-2)
• EPA Substance Registry System: 5'-O-(4,4'-DiMethoxytrityl)-N6-Phenoxyacetyl adenosine(121076-16-2)

Safety Data

• Hazardous Substances Data: 121076-16-2(Hazardous Substances Data)

Upstream product

• 701-99-5 Phenoxyacetyl chloride 
• 10457-15-5 O^2'_,O3'_,O5'-tris-trimethylsilanyl-adenosine 
• 17331-18-9 N'-[9-((3aR,4R,6R,6aR)-2-Dimethylamino-6-hydroxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-N,N-dimethyl-formamidine 
• 57018-82-3 5'-O-dimethoxytrityladenosine 
• 375345-66-7 phenoxyacetyl-1-O-benzotriazolide 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 119824-65-6 N⁶-phenoxyacetyladenosine 
• 58-61-7 adenosine 

Downstream Products

• 1097131-05-9 5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-N⁶-phenoxyacetyl-adenosine 
• 1146634-31-2 5'-O-(4,4'-dimethoxytrityl)-3'-O-pivaloyloxymethyl-N⁶-phenoxyacetyl-adenosine 
• 1450897-41-2 C₅₅H₅₅N₅O₁₅ 
• 1450897-38-7 5'-O-(4,4'-dimethoxytrityl)-3'-O-pivaloyloxymethyl-2'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)-N⁶-phenoxyacetyl-adenosine 
• 129395-58-0 C₅₀H₆₀N₇O₈PSSi 
• 121058-86-4 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 
• 121058-83-1 5′-O-(dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-N⁶-phenoxyacetyladenosine 
• 157567-73-2 N-{9-[(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-furan-2-yl]-9H-purin-6-yl}-2-phenoxy-acetamide 

Relevant articles and documents

A base-labile group for 2′-OH protection of ribonucleosides: A major challenge for RNA synthesis

A base-labile group for 2'-OH protection of ribonucleosides was investigated. The solid support was dried by blowing argon through a DNA synthesizer and was first treated with 10% anhydrous piperidine in CH 3CN at room temperature for 15 minutes to eliminate cyanoethyl groups from phosphates. The piperidine solution was removed from the column and the solid support was washed with CH3CN. The three ammoniacal eluates were collected in a screw-capped glass vial and were left at room temperature for a further 1.5 hours to completely deprotect nucleobases and 2'-hydroxyl groups. The fully deprotected oligonucleotide was transferred to a 50 mL round-bottomed flask and isopropylamine was added to the solution before evaporation to dryness. It was observed that PivOM method provides highly pure RNA without any additional desalting step.

THE USE OF LABILE BASE PROTECTING GROUPS IN OLIGORIBONUCLEOTIDE SYNTHESIS

The use of phenoxyacetyl group for the protection of the exocyclic amino function of purine bases and acetyl group for cytosine in oligonucleotide synthesis by the cyanoethylphosphoramidite approach is described.A side reaction - i.e. partial replacement of phenoxyacetyl group of protected guanines by acetyl group - was observed during the capping step.It can be avoided by the use of phenoxyacetic anhydride in place of acetic anhydride.