2140-71-8

Usage

Uses

Used in Pharmaceutical Industry:
2'-O-Methylguanosine is used as a guanosine analog for the preparation of nucleoside derivatives, which act as inhibitors of RNA-dependent RNA viral polymerase. This application is crucial in the development of antiviral therapies targeting RNA viruses.
Used in Biochemical Research:
As a modified nucleoside, 2'-O-Methylguanosine is utilized in biochemical research to study the role of modified nucleosides in the stabilization of tRNA and rRNA structures, as well as their potential effects on cellular processes such as apoptosis.

Upstream product

• 17287-03-5 trimethylsulphonium hydroxide 
• 118-00-3 G 
• 188658-55-1 6-(tert-Butyl-diphenyl-silanyloxy)-9-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-methoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-9H-purin-2-ylamine 
• 473278-52-3 2-Amino-9-((2R,3R,3aS,9aR)-3-hydroxy-5,5,7,7-tetraisopropyl-hexahydro-1,4,8-trioxa-5,7-disila-cyclopentacycloocten-2-yl)-1,9-dihydro-purin-6-one 
• 80791-87-3 2-amino-2'-O-methyladenosine 
• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 
• 194034-59-8 2-amino-6-chloro-9-[2'-O-methyl-β-D-ribofuranosyl]purine 
• 1061667-19-3 8-thio-2'-O-methylguanosine 
• 684-93-5 1-methyl-1-nitrosourea 
• 2096-10-8 adenosine-2-amine 
• 185761-02-8 2'-O-methyl-5'-O-(monomethoxytrityl)-N²-<2-(4-nitrophenyl)ethoxycarbonyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanosine 
• 188658-54-0 6-O-(tert-Butyldiphenylsilyl)-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)guanosine 
• 69304-44-5 3',5'-O-1,1,3,3-tetraisopropyldisiloxan-1,3-diyl-guanosine 
• 2004-07-1 2-Amino-6-chloropurine riboside 

Downstream Products

• 183737-04-4 N₂-dimethylaminomethylene-2'-O-methylguanosine 
• 444019-11-8 N²-(4-monomethoxytrityl)-2'-O-methylguanosine 
• 215190-95-7 Pent-4-enoic acid (9-{(2R,3R,4R,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-methoxy-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-amide 
• 63264-29-9 N²-isobutyryl-2′-O-methylguanosine 
• 135023-21-1 N²,2’-O-dimethylguanosine 
• 1613530-50-9 C₂₃H₂₇N₅O₇S 

Relevant academic research and scientific papers

Noncanonical RNA Nucleosides as Molecular Fossils of an Early Earth—Generation by Prebiotic Methylations and Carbamoylations

The RNA-world hypothesis assumes that life on Earth started with small RNA molecules that catalyzed their own formation. Vital to this hypothesis is the need for prebiotic routes towards RNA. Contemporary RNA, however, is not only constructed from the four canonical nucleobases (A, C, G, and U), it also contains many chemically modified (noncanonical) bases. A still open question is whether these noncanonical bases were formed in parallel to the canonical bases (chemical origin) or later, when life demanded higher functional diversity (biological origin). Here we show that isocyanates in combination with sodium nitrite establish methylating and carbamoylating reactivity compatible with early Earth conditions. These reactions lead to the formation of methylated and amino acid modified nucleosides that are still extant. Our data provide a plausible scenario for the chemical origin of certain noncanonical bases, which suggests that they are fossils of an early Earth.

PROCESS FOR THE SYNTHESIS OF 2'-O-SUBSTITUTED PURINES

The present invention provides an improved process for the synthesis of 2′-O-substituted purine nucleosides. The process includes anhydro or thioanhydro ring opening of a selected 8,2′-cyclopurine nucleoside with a weak nucleophile in the presence of a Lewis acid ester, followed by reduction to afford the desired 2′-O-substituted purine nucleoside.

An efficient process for synthesis of 2′-O-methyl and 3′-O-methyl guanosine from 2-aminoadenosine using diazomethane and the catalyst stannous chloride

An improved strategy for the selective synthesis of 2′- O -methyl and 3′- O -methyl guanosine from 2-aminoadenosine is reported by using the catalyst stannous chloride. The regioselectivity of the 2′ and 3′- O -alkylation was achieved by optimizing the addition, timing, and concentration of the catalysts and diazomethane during the methylation reaction. An efficient and selective alkylation at 2′-OH of 2-aminoadenosine was achieved by mixing a stoichiometric amount of stannous chloride at room temperature in DMF. The reaction mixture was stirred at 50°C for 1 min and immediately followed by addition of diazomethane. The resulting 2′- O -methyl 2-aminoadenosine was treated with the enzyme adenosine deaminase, which resulted in an efficient conversion to the desired 2′- O -methylguanosine (98% yield). The product was isolated by crystallization. In contrast, the methylation at 3′-OH of 2-aminoadenosine was achieved by mixing a stoichiometric amount of stannous chloride in DMF and stirring at 50°C for 15 min, followed by addition of diazomethane. The resulting mixture containing 3′- O -methyl-2- aminoadenosine in 90% yield and 2′- O -methyl-2-aminoadenosine in 10% yield was treated with the enzyme adenosine deaminase, which preferentially deaminated only 3′- O -methyl-2-aminoadenosine, resulting in the production of 3′- O -methylguanosine in 88% yield. Due to the extremely low solubility 3′- O -methylguanosine, the compound precipitated and was isolated by centrifugation. This synthetic route obviates the chromatographic purification. Selective monomethylation is achieved by using the unprotected ribonucleoside. As a result, the method described herein represents a significant improvement over the current synthetic approach by providing superior product yield and economy, a much more facile purification of 2′,3′- O -methylated isomers, and eliminating the need for protected ribonucleosides reagents. Copyright Taylor & Francis Group, LLC.

MDPSCL2: a new protecting group for chemoselective synthesis of 2'-O-alkylated guanosines.

An improved strategy for the synthesis of 2'-O-methyl-guanosine (6) and 2'-MOE-guanosine (8) is reported. The regioselectivity of the alkylation was attained using a novel silicon-based protecting group, methylene-bis (diisopropyl-silylchloride) (MDPSCl2, 2). The alkylation proceeded in a chemoselective manner using NaHMDS as the base and MeCl or MOE-Br as the appropriate electrophiles.

Novel synthesis of 2′-O-methylguanosine

An efficient and chemoselective synthesis of 2′-O-methylguanosine (6) has been accomplished in high yield without protection of the guanine base. The salient feature of the synthesis of 6 lies in the application of methylene-bis-(diisopropylsilyl chloride), (MDPSCl2, 2) as a new 3′,5′-O-protecting group for nucleosides. Use of CH3Cl as a weak electrophile and NaHMDS as a mild base was crucial to the success of the 2′-O-methylation of 3′,5′-O-protected guanosine.

Nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase

The present invention provides nucleoside compounds and certain derivatives thereof which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-dependent RNA viral infection. They are particularly useful as inhibitors of hepatitis C virus (HCV) NS5B polymerase, as inhibitors of HCV replication, and/or for the treatment of hepatitis C infection. The invention also describes pharmaceutical compositions containing such nucleoside compounds alone or in combination with other agents active against RNA-dependent RNA viral infection, in particular HCV infection. Also disclosed are methods of inhibiting RNA-dependent RNA polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection with the nucleoside compounds of the present invention.

Improved synthetic approaches toward 2'-O-methyl-adenosine and guanosine and their N-acyl derivatives

We developed several improved approaches toward 2'-O-methyl adenosine and guanosine and their N-acyl derivatives. (a) Transglycosylation of N4- acetyl-5', 3'-di-O-acetyl-2'-O-methyl cytidine with N6-Bz-adenine provided N6-benzoyl-5'3'-di-O-acetyl-2'-O-methyl adenosine in 50% yield. (b) Regioselective methylation of 2-amino-6-chloro purine riboside with MeI/NaH followed by hydrolysis provided 2'-O-Me-guanosine in high yield. The same 2'- O-Me-precursor was transformed into 2'-O-Me-adenosine in 58% yield. (c) Very efficient transformation of 2,6-diamino-purine riboside into N2-isobutyryl (isopropylphenoxyacetyl) 2'-O-Me-guanosine through methylation of 5',3'-O- TIPDSi derivative followed by selective N2-acylation, deamination and desylilation provided target compounds in 70% combined yield. (d) Mg2+ and Ag+ directed methylation of N1-Bzl-guanosine proceeded in >80% yield with ratio of 2'-O-Me-3'-O-Me=9:1. The same methylation of adenosine with Ag+ and Sr2+ acetylacetonates provided 2'-O-Me-adenosine in 75-80% yield. (C) 2000 Elsevier Science Ltd.

Chemical syntheses of 2'-O-methoxy purine nucleosides

Several processes for the chemical synthesis of 2'-O-methoxy purine nucleosides are herein disclosed.

2'-O-alkylnucleotides as well as polymers which contain such nucleotides

Oligonucleotides having the general formula, STR1 in which B denotes an arbitrary nucleobase, A equals 0 or CH2 ; X or Z equals O, S, NH or denotes CH2 whereby X and Z can be the same or different, V and W denote O, S, Se, NH2/

Protection of the guanine residue during synthesis of 2'-O-alkyl-guanosine derivatives

Highly selective 2'-O-alkylation of 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)guanosine has been achieved by using an alkyl halide and a sterically hindered strong organic base, when the 6-O atom is protected with either a 2-nitrophenyl or a tert-butyldiphenylsilyl group prior to the alkylation.A minimum of chromatography is required, the yields are high and none of the unwanted isomer is produced.Moreover, the highly versatile intermediates enable the synthesis of several new 2'-O-alkylguanosine derivatives as well as base-modified analogues.