10300-22-8

Basic information

• Product Name: 3'-O-Methyl-D-adenosine
• Synonyms: 3'-O-Methyl-D-adenosine;3'-OMe-A
• CAS NO: 10300-22-8
• Molecular Formula: C₁₁H₁₅N₅O₄
• Molecular Weight: 281.2679
• Mol File: 10300-22-8.mol

Chemical Properties

• Melting Point: 177-178 °C
• Boiling Point: 623.8 °C at 760 mmHg
• Flash Point: 331 °C
• Appearance: /
• Density: 1.84 g/cm³
• PKA: 12.98±0.70(Predicted)
• CAS DataBase Reference: 3'-O-Methyl-D-adenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-O-Methyl-D-adenosine(10300-22-8)
• EPA Substance Registry System: 3'-O-Methyl-D-adenosine(10300-22-8)

Safety Data

• Hazardous Substances Data: 10300-22-8(Hazardous Substances Data)

Usage

Physical Form

Solid

Application

3'-O-Methyladenosine is a useful research chemical compound.

Upstream product

• 512-56-1 trimethyl phosphite 
• 58-61-7 adenosine 
• 17287-03-5 trimethylsulphonium hydroxide 
• 1899-02-1 trimethylphenylammonium hydroxide 
• 74230-06-1 trimethylselenonium hydroxyde 
• 74-88-4 methyl iodide 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 80-48-8 methyl p-toluene sulfonate 
• 647834-80-8 O-levulinyl acetonoxime 

Downstream Products

• 60037-52-7 N⁶,O^3'-methyladenosine 
• 20649-46-1 2'-O,3'-O-dimethyladenosine 
• 185761-10-8 3'-O-methyl-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 
• 2140-79-6 2'-O-methyl adenosine 
• 1166393-97-0 5'-O-[ (tert-butyl)(dimethyl)silyl]-N₆-[(4-methoxyphenyl)(diphenyl)methyl]-3'-O-methyladenosine 
• 1166393-98-1 C₄₂H₅₁N₅O₇Si 
• 1166393-99-2 2'-O-levulinoyl-N₆-[(4-methoxyphenyl)(diphenyl)methyl]-3'-O-methyladenosine 
• 1166394-11-1 C₄₄H₅₆N₇O₇P 
• 1373756-00-3 2'-O-levulinoyl-N₆-[(4-methoxyphenyl)(diphenyl)methyl]-3'-O-methyladenosine 5'-(bis{3-[(acetyloxy)methoxy]-2,2-bis(ethoxycarbonyl)propyl} phosphate) 
• 1373756-01-4 C₅₅H₆₈N₅O₂₂P 
• 1388227-08-4 C₆₃H₈₇N₇O₂₂P₂ 

Relevant articles and documents

Selective 2'-O-Methylation of Pyrimidine-Ribonucleosides by Trimethylsulfonium Hydroxide in the Presence of Mg2+ and Ca2+ Ions

Reactions of various ribonucleosides with trimethylsulfonium hydroxide were investigated in the presence of Mg2+ and Ca2+ ions.The 2'-OH groups of pyrimidine-ribonucleosides were methylated selectively.

Improved synthesis and isolation of 2'-O-methyladenosine: Effective and scalable enzymatic separation of 2'/3'-O-methyladenosine regioisomers

An efficient separation of a mixture of 2'/3'-O-methyladenosine regioisomers (1 + 2: 1:1) has been developed by selective enzymatic acylation using immobilized Pseudomonas cepacia lipase (PSL-C) in combination with acetonoxime levulinate as acyl donor. Th

Solid-phase synthesis of carbohydrate and phosphodiester modified 2'-5' oligoadenylate analogs

A series of 2'-5' oligoadenylate analogs containing internucleotide and ribose modifications were prepared by solid-phase methods as potential interferon mimetics. All syntheses were carried out using automated methodologies with precursors that allow for the generation of multiple combinations of modification.

Synthesis and Conformational Analysis of Phosphate-Methylated RNA Dinucleotides

Synthesis of RNA dimers having a methyl phosphotriester group as the internucleoside linkage is reported; six pairs of diastereoisomerically pure systems were prepared, i.e., r(CpU) (15), r(ApU) (16), r(CpC) (17), r(ApC) (18), r(CpG) (19), and r(ApG) (20).Compounds 15-20 are stabilized by a 2'-O-methyl group in the 5'-terminal residue.The present systems represent the third class of backbone-modified RNA oligomers, following the 2'-O-methylribonucleotide phosphorothioates and the 2'-O-methylribonucleotide methyl phosphonates.Our synthetic approach comprises the use of 9-fluorenylmethoxycarbonyl (Fmoc) groups for transient protection of the exocyclic NH2 groups of the bases A, C, and G, levulinoyl (Lev) groups for the transient protection of the 2'- and 3'-OH groups of the 3'-terminal residue, methanolic K2CO3 for the simultaneous removal of Fmoc and Lev groups with full preservation of the methyl phosphotriester function, and finally reversed-phase HPLC separation of the SP and RP diastereoisomers.The availability of the six dimers in diastereoisomerically pure form enabled us to examine the molecular conformation using high-field NMR and circular dichroism (CD) spectroscopy.These studies led to the following conclusions: (i) NMR J-coupling analysis: the central C4'-C5' (γ) and C5'-O5' (β) bonds in 15-20 show less preference for the γ+ and βt rotamers, in comparison with their natural analogues, i.e., base stacking is diminished upon introduction of the two methyl groups on O2' and on the phosphate group; (ii) CD analysis: 15-20 show substantially reduced molecular ellipticities when compared to the natural counterparts, which also reveals that base stacking is reduced; (iii) UV and variable-temperature 1H NMR measurements: (SP)- and (RP)-19 show self-association, via the formation of a right-handed miniduplex with two C-G base pairs ((SP)-19, Tm = 9.3 deg C, concn = 36.6 μM; (RP)-19, Tm = 8.7 deg C, concn = 48.1 μM).The present conformational data on (RP)- and (SP)-15-20 are in agreement with literature data on other phosphate-triesterified oligonucleotides, e.g., the trimer d(TPOEtGPOEtG) and the tetramer d(TPOEtTPOEtCPOEtA).While the latter systems also showed little base-base stacking, it was estabished that they readily form a local duplex with a complementary natural RNA sequence.Hence we anticipate that phosphate-methylated 2'-O-methyl RNA oligomers, longer than the dimer systems described in the present work, will also hybridize easily with complementary natural RNA.

Methylation of Adenosine and Related Nucleosides with Trimethylselenonium Hydroxyde, and Regiospecific Effects of Copper(II) Ions

Methylation of adenosine, deoxyadenosine, 6-N-methyladenosine and 2'(3')-O-methyladenosines with trimethylselenonium hydroxyde was studied in the presence and absence of copper(II) acetylacetonate .It was found that copper(II) ions promoted methylation of the 2'(3')-OH groups of the ribonucleosides but suppressed methylation at the N-1 position of the adenine rings.The metal-ion effects are discussed in conjunction with a catalytic role for Cu(AA)2 in the reactions.

The Methylation of Ribonucleosides by Trimethyl Phosphate or Dimethyl Sulfate in the Presence of Boric Acid

Uridine, inosine, adenosine, and thymidine were methylated selectively at the base moieties by the use of trimethyl phosphate or dimethyl sulfate in the presence of boric acid.A suppressing effect of boric acid on the methylation of the ribose-hydroxyl groups was discussed briefly.

Methylation of Nucleosides with Trimethylsulfonium Hydroxide. Effects of Transition Metal Ions

The effect of transition metal acetylacetonates on the methylation of ribo- and deoxyribonucleosides with trimethylsulfonium hydroxide was studied.With ribonucleosides the metal complexes promoted O'-methylation at the 2' and 3' positions of the ribosyl group.A comparable effect was not observed in methylation of deoxyribonucleosides.These results are attributed to an increase in the nucleophilicity of the 2'-OH and 3'-OH groups of the ribosides through complex formation with the metal ion; such a complex cannot form with the deoxyribose derivatives.The activity of the metal ions studied for promoting this O'-methylation increased in the order Mn2+ 2+ = Zn2+ 2+ 2+ 3+.These M(AA)n also suppressed N-methylation of the purine and pyrimidine rings of adenosine and cytidine.It is suggested that this result may be caused by coordination of the metal ions with ring nitrogens.

Methylation study of ribonucleosides, deoxyribonucleosides, and 2′-O-methylribonucleosides with trimethylsulphonium hydroxide and trimethylsulphonium iodide. Influence of the 2′-hydroxy-groups on the reactivity of the base moieties of ribonucleosides

Methylations of the naturally occuring ribonucleoside (1), deoxyribonucleoside (2), and 2′-O-methylribonucleoside (3) were carried out using trimethylsulphonium hydroxide (Me3SOH) and trimethylsulphonium iodide (Me3Sl). The base moiety of (2) and (3) are more reactive than the corresponding base moiety of (1). The sites and extent of methylation of (2) are considerably different from those of (1), but are almost identical with those of (3). The reactivities of (1)-(3) are discussed in connection to an intramolecular interaction of the 2′-OH groups with the base moiety of (1). The methylating characteristics of Me 3SOH and Me3Sl are also described. The kinetics indicate an SN2 mechanism for methylation of nucleosides by Me 3S+ ions.