152774-16-8

Basic information

• Product Name: Adenosine-9-yl acetic acid t-butyl ester
• Synonyms: Adenosine-9-yl acetic acid t-butyl ester;Adenin-9-yl acetic acid t-butyl ester;tert-butyl 2-(6-amino-9H-purin-9-yl)acetate;9H-Purine-9-acetic acid, 6-amino-, 1,1-dimethylethyl ester;6-Amino-9H-purine-9-acetic acid t-butyl ester
• CAS NO: 152774-16-8
• Molecular Formula: C₁₁H₁₅N₅O₂
• Molecular Weight: 382.39166
• Mol File: 152774-16-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Adenosine-9-yl acetic acid t-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Adenosine-9-yl acetic acid t-butyl ester(152774-16-8)
• EPA Substance Registry System: Adenosine-9-yl acetic acid t-butyl ester(152774-16-8)

Safety Data

• Hazardous Substances Data: 152774-16-8(Hazardous Substances Data)

Upstream product

• 107-59-5 tert-Butyl chloroacetate 
• 73-24-5 7H-purin-6-ylamine 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 66224-66-6 adenine 

Downstream Products

• 202127-95-5 (6-Benzoylamino-purin-9-yl)-acetic acid tert-butyl ester 
• 20128-29-4 2-(6-amino-9H-purin-9-yl)acetic acid 
• 171486-04-7 N⁶-(benzoyl)-9-(carboxymethyl)adenine 

Relevant articles and documents

Synthesis of nucleobase-caged peptide nucleic acids having improved photochemical properties

A nucleobase-caged peptide nucleic acid (PNA) having a (6-bromo-7- methoxycoumarin)-4-ylmethoxycarbonyl (Bmcmoc) caging group was newly synthesized. The Bmcmoc-caged PNAs were photolyzed to produce parent PNAs with a high photochemical efficiency. Introduction of a single Bmcmoc group was sufficient to suppress polymerase chain reaction (PCR) clamping activity and triplex invasion complex formation. Photo-mediated restoration of the PCR clamping activity was also demonstrated.

Synthesis of potential purinoceptor antagonists: Application of P1-tBU phosphazene base for alkylation of adenine in solution and on solid phase

Alkylation of adenine in solution and on solid phase was accelerated by phosphazene base P1-tBu compared to mineral bases. The reactions in solution afforded regioselectively the appropriate N9-alkylated adenines with high preparative yields while the rea

Oligonucleotide analogues with 4-hydroxy-N-acetylprolinol as sugar substitute

Modified oligonucleotides incorporating trans-4-hydroxy-N-acetyl-L-prolinol (trans-4-HO-L-NAP) or its D-analogue as sugar substitute were synthesised with adenine and thymine as nucleobases. All-adenine oligonucleotides built from (2S,4S) or (2R,4R)-cis-4

Nucleosides and Oligonucleotides Derived from trans-4-Hydroxy-N-acetylprolinol

The 4-O-phosphoramidites of monomethoxytritylated 4-hydroxy-N-6-benzoyladenin-9-yl)acetyl>prolinol and 4-hydroxy-N-prolinol were prepared for incorporation into nucleic acids.The L-trans all-adenine oligonucleotide (ON) hybridises to natural oligothymidylate, apparently via triplex formation.All-purine sequences of the L-trans form can also form homo-complexes with their pyrimidine counterpart.The D-trans compounds give larger destabilisation when inserted in DNA.D-trans all-adenine ONs do not form complexes with natural oligothymidylate.For this series of modified ONs no hybridisation could be detected between complementary strands of opposite enantiomeric form.

Heterocyclic Ambident Nucleophiles. III* The Alkylation of Sodium Adenide

The alkylation of sodium adenide in HCONMe2 (30 deg) with various alkylating agents was analysed by 1H n.m.r. spectroscopy.Widely varying N3:N7:N9 alkylation patterns were observed, depending on the alkylating agent.These patterns are interpreted in terms of the electrostatic, thermodynamic and steric factors involved in the different SN2 transition states appropriate to each alkylating agent.Hydrogen bonding association between the 6-amino group and certain carbonyl containing alkylating agents is proposed to explain the enhancedN7-alkylation in some cases.Support for this latter proposal was obtain from a comparison of the adenine alkylation results with the corresponding alkylation patterns of 6-pivaloylamino- and 6-chloro-purine.

Heterocyclic Ambident Nucleophiles. IV* The alkylation of Metal Salts of Adenine

The N3:N7:N9 alkylation patterns for reactions of the lithium, sodium, and potassium salts of adenine with various alkylating agents in dimethyl sulfoxide were determined by 1H n.m.r. spectroscopy.Only for the Li+ salt was any significant effect of ionic association noticed.Of the alkylating agents used, only chloromethyl pivalate gave a concentration dependent alkylation pattern.The latter effect was most pronounced with the heterogenous alkylation conditions of anhydrous Na2CO3/HCONMe2, adenine, and chloromethyl pivalate; here, increasingconcentrations changed the main reaction from N7- to N9-alkylation.Solvent effects on the alkylation patterns were also studied.Within the common dipolar aprotic solvent group, (Me2N)3PO, HCONMe2 and Me2SO, effects were small; in protic solvents, particularly formamide, enhanced N3-alkylation was observed.