168427-74-5

Basic information

• Product Name: 2'-O-MOE-ADENOSINE
• Synonyms: 2'-O-MOE-ADENOSINE;2'-O-(2-METHOXYETHYL)ADENOSINE;Adenosine, 2'-O-(2-Methoxyethyl)-;(2R,3R,4R,5R)-5-(6-AMino-9H-purin-9-yl)-2-(hydroxyMethyl)-4-(2-Methoxyethoxy)tetrahydrofuran-3-ol;(2R,3R,4R,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxy-methyl)-4-(2-methoxyethoxy)tetrahydrofuran-3-o;(2R,3R,4R,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxy-methyl)-4-(2-methoxyethoxy)tetrahydrofuran-;2'-O-MOE-A;2'-O-Methoxyethyl-adenosine
• CAS NO: 168427-74-5
• Molecular Formula: C₁₃H₁₉N₅O₅
• Molecular Weight: 325.32
• EINECS: 500-100-4
• Product Categories: Bases & Related Reagents;Carbohydrates & Derivatives;Heterocycles;Nucleotides
• Mol File: 168427-74-5.mol

Chemical Properties

• Boiling Point: 638.954 °C at 760 mmHg
• Flash Point: 340.227 °C
• Appearance: /
• Density: 1.701 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.72
• Storage Temp.: 2-8°C(protect from light)
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 13.12±0.70(Predicted)
• CAS DataBase Reference: 2'-O-MOE-ADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-O-MOE-ADENOSINE(168427-74-5)
• EPA Substance Registry System: 2'-O-MOE-ADENOSINE(168427-74-5)

Safety Data

• Hazardous Substances Data: 168427-74-5(Hazardous Substances Data)

Usage

Uses

A adenosine derivative as building blocks for cross-linking oligonucleotides.

InChI:InChI=1/C13H19N5O5/c1-21-2-3-22-10-9(20)7(4-19)23-13(10)18-6-17-8-11(14)15-5-16-12(8)18/h5-7,9-10,13,19-20H,2-4H2,1H3,(H2,14,15,16)/t7-,9+,10+,13-/m1/s1

Upstream product

• 168427-73-4 3',5'-Bis-O-(2,4-dichlorobenzyl)-2'-O-(2-methoxyethyl)adenosin 
• 4296-15-5 2-iodo-1-methoxyethane 
• 58-61-7 adenosine 
• 440327-54-8 3',5'-di-O-levulinyl-2'-O-(2-methoxyethyl)adenosine 
• 163759-40-8 methyl 2,3,5-tris-O-(2,4-dichlorobenzyl)-β-D-ribofuranoside 
• 16427-44-4 2-methoxyethyl methanesulfonate 
• 6482-24-2 2-Bromoethyl methyl ether 
• 17178-10-8 2-methoxy-ethyl p-toluenesulfonyloxy ester 
• 168427-69-8 2-O-Acetyl-3',5'-bis-O-(2,4-dichlorobenzyl)inosin 
• 168427-70-1 9-<2'-O-Acetyl-3',5'-bis-O-(2,4-dichlorobenzyl)-β-D-ribofuranosyl>-6-chloro-9H-purin 
• 168427-71-2 9-<3',5'-Bis-O-(2,4-dichlorobenzyl)-β-D-ribofuranosyl>-6-methoxy-9H-purin 
• 163759-42-0 Methyl-2-O-acetyl-3,5-bis-O-(2,4-dichlorobenzyl)-α-D-ribofuranosid 
• 168427-35-8 (3R,4S,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxytetrahydrofuran-3-ol 
• 50-69-1 D-ribose 

Downstream Products

• 251647-48-0 5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-N6-benzoyladenosine 
• 333335-93-6 2'-O-methoxyethyl- N⁶-benzoyl -adenosine 

Relevant articles and documents

Synthesis and cellular activity of stereochemically-pure 2′-O-(2-methoxyethyl)-phosphorothioate oligonucleotides

Stereochemically-pure 2′-O-(2-methoxyethyl)-phosphorothioate (PS-MOE) oligonucleotides were synthesized from new chiral oxazaphospholidine-containing nucleosides. Thermal stability studies showed that the incorporation of Rp-PS linkages increased RNA-binding affinity. In cells, a full Rp-PS-MOE splice-switching oligonucleotide targeting part of the ferrochelatase gene was more potent than its Sp-PS counterpart, but of similar potency to the stereorandom PS-parent sequence.

2'-O-MOE-3'-H-phosphorothioate nucleoside monomer and synthetic method thereof

The invention discloses 2'-O-MOE-3'-H-phosphorodithioate ribonucleotide and 2'-O-MOE-3'-H-phosphorothioate ribonucleotide and precursor compounds thereof, preparation methods and applications of the 2'-O-MOE-3'-H-phosphorodithioate ribonucleotide and the

2 the [...] -O-(2- armor oxygen ethyl) adenosine and 2 the [...] -O-(2- armor oxygen ethyl) guanosine and its derivatives preparation and its purification method

The invention discloses 2'-O-(2-methoxyethyl)adenosine and 2'-O-(2-methoxyethyl)guanosine, preparation of derivatives thereof and purifying methods thereof. The invention provides a preparation method of a compound shown as a formula A. The method compris

Synthesis study of 2′-O-(2-methoxyethyl)-purine derivatives

Alkylation of adenosine and 2-aminoadenosine was studied in dimethylsulfoxide with application of 1-methanesulfonyloxy-2-methoxyethane as an alkylating agent and t-BuOK, KOH and NaH as bases under mild heating. Using new reaction conditions, the improved synthesis of 2′-O-MOE-purine derivatives is described. Copyright Taylor & Francis Group, LLC.

Phosphorus containing cyclic nucleotides

The invention relates to a compound of formula (I) Wherein: B is adenine, guanine or hypoxanthine Z is hydrogen or a negative charge R is —[CH2CH(R1)—O]n—R2, —CH2CH2X, in which R1is hydrogen or (C1-C6) alkyl R2is hydrogen or (C1-C6) alkyl n is a number from 1 to 6 X is OH, F, NR3R4 R3and R4are independently from each other hydrogen or (C1-C6) alkyl and to methods of enzymatically treating these compounds with biocatalysts having cyclic phosphodiesterase activity.

Building blocks for the solution phase synthesis of oligonucleotides: Regioselective hydrolysis of 3′,5′-di-O-levulinylnucleosides using an enzymatic approach

A short and convenient synthesis of 3′- and 5′-O-levulinyl-2′-deoxynucleosides has been developed from the corresponding 3′,5′-di-O-levulinyl derivatives by regioselective enzymatic hydrolysis, avoiding several tedious chemical protection/deprotection steps. Thus, Candida antartica lipase B (CAL-B) was found to selectively hydrolyze the 5′-levulinate esters, furnishing 3′-O-levulinyl-2′-deoxynucleosides 3 in >80% isolated yields. On the other hand, immobilized Pseudomonas cepacia lipase (PSL-C) and Candida antarctica lipase A (CAL-A) exhibit the opposite selectivity toward the hydrolysis at the 3′-position, affording 5′-O-levulinyl derivatives 4 in >70% yields. A similar hydrolysis procedure was successfully extended to the synthesis of 3′- and 5′-O-levulinyl-protected 2′-O-alkylribonucleosides 7 and 8. This work demonstrates for the first time application of commercial CAL-B and PSL-C toward regioselective hydrolysis of levulinyl esters with excellent selectivity and yields. It is noteworthy that protected cytidine and adenosine base derivatives were not adequate substrates for the enzymatic hydrolysis with CAL-B, whereas PSL-C was able to accommodate protected bases during selective hydrolysis. In addition, we report an improved synthesis of dilevulinyl esters using a polymer-bound carbodiimide as a replacement for dicyclohexylcarbodiimide (DCC), thus considerably simplifying the workup for esterification reactions.

Investigations on the influence of 2'-O-alkyl modifications on the base pairing properties of oligonucleotides

The antisense strategy has gained wide acceptance as a promising drug development concept. Antisense drugs hybridize with selected complementary sequences in a highly specific manner. However, as a main prerequisite for extensive therapeutic use of this new class of drugs, selected structural modifications are required to adjust pharmacokinetic and pharmacodynamic behavior. In continuation of our earlier investigations on 2'-O-modified oligonucleotides (Gotten, M., Oberhauser, B., Brunar, H., Holzner, A., Issakides, G., Noe, C.R., Schaffer, G., Wagner, E., Bimstiel, M.L., 1991. 2'-O-methyl, 2'-O-ethyl oligoribonucleotides and phosphorothioate oligodeoxyribonucleotides as inhibitors of the in vitro U7 snRNP-dependent mRNA processing event. Nucleic Acids Res. 19, 2629-2635; Wagner, E., Oberhauser, B., Holzner, A., Brunar, H., Issakides, G., Schaffner, G., Gotten, M., Knollmuller, M., Noe, C.R., 1991. A simple procedure for the preparation of protected 2'-O-methyl or 2'-O-ethyl ribonucleoside-3'-O-phosphoramidites. Nucleic Acids Res. 19, 5965-5971) further series of modified oligonucleotides containing different modified 2'-O-adenosines have been synthesized. On the one hand linear alkyl moieties of increasing length, on the other hand oxyethylene moieties of corresponding length were introduced at the 2'-O-position of adenosine. Following another approach a cationic charge was introduced by insertion of an aminohexylmodification at the 2'-O-position of adenosine (Brunar, H., Haberhauer, G., Werner, D., Noe, C.R., 1994. 2'-O-Modified oligonucleotides: Synthesis and biophysical analysis. Eur. J. Pharm. Sci. 2, 150). Molecule dynamics simulations had shown that this cationic modification upon duplex formation leads to both intra- and interstrand interactions. To determine the influence of the different modifications, such as cationic charge, alkyl chainlength and introduction of oxygen into the chain, on duplex stability melting temperatures were measured by recording circular dichroism versus temperature.

38. A new access to 2'-O-alkylated ribonucleosides and properties of 2'-O-alkylated oligoribonucleotides

A general access to 2'-O-alkylated ribonucleosides using the key intermediate 5 is presented. The incorporation of 2'-O-'ethyleneglycol'- and 2'-O-'glycerol'-substituted (i.e., 2'-O-(2-hydroxyethyl)- and 2'-O-(2,3-dihydroxypropyl)-substituted) ribonucleosides into oligonucleotides affords a new generation of oligonucleotides with high affinity for RNA, high specificity, and increased nuclease resistance.