2140-72-9

Usage

Uses

Used in Pharmaceutical Industry:
2'-O-Methylcytidine is used as a nucleoside derivative for the development of antiviral agents targeting RNA-dependent RNA viral polymerase. This application is crucial in the treatment and prevention of viral infections, particularly those caused by RNA viruses.
Used in Research and Development:
As a cytidine analog, 2'-O-Methylcytidine is utilized in research and development for studying the structure, function, and mechanisms of RNA and DNA molecules. It aids in understanding the role of modified nucleosides in various biological processes and their potential applications in medicine and biotechnology.

Synthetic route

3',5'-di-O-acetyl-2'-O-methylcytidine (1085342-86-4) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With ammonia In methanol at 20℃;	99%

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methylcytidine (97626-19-2) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;	96%

N4-benzoyl-3',5'-di-O-benzoyl-2'-O-methylcytidine (73793-16-5) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With ammonia In methanol at 4℃; for 48h;	80%

magnesium ethylate (2414-98-4) + 2,2'-anhydrocytidine hydrochloride → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
In methanol for 5h; Reflux;	76%

diazomethane (186581-53-3, 908094-01-9) + CYTIDINE (65-46-3) → 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With tin(ll) chloride In methanol; 1,2-dimethoxyethane for 0.333333h; Ambient temperature;	A 14% B 69%
dibutyldimethoxytin In methanol Mechanism;
dibutyldimethoxytin In methanol

trimethylsulphonium hydroxide (17287-03-5) + CYTIDINE (65-46-3) → 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9) + N3-methylcytidine (2140-64-9)

Conditions	Yield
With copper acetylacetonate In N,N-dimethyl-formamide at 70℃; for 1h;	A 22% B 60% C 3%
In N,N-dimethyl-formamide at 70℃; for 1h;	A 7% B 28% C 13%
With copper acetylacetonate In N,N-dimethyl-formamide at 70℃; for 1h; Product distribution; without metallo-organic compound;
In methanol; N,N-dimethyl-formamide at 70℃; for 1h; Title compound not separated from byproducts;	A 7 % Spectr. B 28 % Spectr. C 13 % Spectr.
In methanol; N,N-dimethyl-formamide at 70℃; Title compound not separated from byproducts;	A n/a B 28 % Spectr. C 13 % Spectr.

trimethylsulphonium hydroxide (17287-03-5) + CYTIDINE (65-46-3) → 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With magnesium(II) acetylacetonate In methanol; N,N-dimethyl-formamide at 70℃; for 1h; Product distribution; absence of metal ion;	A 2% B 43%
With magnesium(II) acetylacetonate In methanol; N,N-dimethyl-formamide at 70℃; for 1h;	A 2% B 43%

trimethylphenylammonium hydroxide (1899-02-1) + CYTIDINE (65-46-3) → 3-methyluridine (2140-69-4) + 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
In N,N-dimethyl-formamide at 100℃;	A n/a B 3 % Spectr. C 24%
In N,N-dimethyl-formamide at 100℃;	A 22 % Spectr. B 4 % Spectr. C 21%

1-methyl-1-nitrosourea (684-93-5) + CYTIDINE (65-46-3) → 2'-O-methylcytidine (2140-72-9) + N3-methylcytidine (2140-64-9)

Conditions	Yield
With borax In water; formamide at 50℃; for 18h;	A 5% B n/a

CYTIDINE (65-46-3) + methyl iodide (74-88-4) → 3'-O-Methylcytidine (20594-00-7) + 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With sodium hydride 1) DMF, 0 deg C, 45 min, 2a) 0 deg C, 2.5 h, 2b) r.t., 1 h; Multistep reaction. Yields of byproduct given;
With sodium hydride 1) DMF, 0 deg C, 45 min, 2a) 0 deg C, 2.5 h, 2b) r.t., 1 h; Yield given. Multistep reaction;

N-{1-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-3-methyl-butyramide → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With dichloro-acetic acid; ammonium hydroxide

Trimethyl borate (121-43-7) + 2,2'-anhydro-1-(β-D-arabinofuranosyl)cytosine acetate (10212-28-9) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
With methanol; boron trifluoride for 48h; Ring cleavage; Heating;

1-(3',5'-O-1,1,3,3-tetraisopropyl-1,3-disilyl)-β-D-ribofuranosyl-4-(2-nitrophenyl)-2-pyrimidinone (108782-90-7) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / silver oxide / acetone / 72 h / 20 °C 2: 75 percent / ammonia / tetrahydrofuran 3: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

1-(3',5'-O-1,1,3,3-tetraisopropyl-1,3-disilyl)-β-D-ribofuranosyl-2'-O-methyl-4-(2-nitrophenyl)-2-pyrimidinone (110567-19-6) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / ammonia / tetrahydrofuran 2: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

4-(2-Nitro-phenoxy)-1-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-trimethylsilanyloxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidin-2-one → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.12 g / p-toluenesulfonic acid / CH2Cl2 / 0.03 h / 20 °C 2: 81 percent / silver oxide / acetone / 72 h / 20 °C 3: 75 percent / ammonia / tetrahydrofuran 4: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-2'-O-(trimethylsilyl)uridine (415903-48-9) → 2'-O-methylcytidine (2140-72-9)

Conditions

Yield

Multi-step reaction with 5 steps 1: 1.) triethylamine, 2-mesitylenesulfonyl chloride, N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane / 1.) dichloromethane, 30 min, 2.) dichloromethane, 60 min 2: 1.12 g / p-toluenesulfonic acid / CH2Cl2 / 0.03 h / 20 °C 3: 81 percent / silver oxide / acetone / 72 h / 20 °C 4: 75 percent / ammonia / tetrahydrofuran 5: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

uridine (58-96-8) + aqueous H3PO4 → 2'-O-methylcytidine (2140-72-9)

Conditions

Yield

Multi-step reaction with 7 steps 1: pyridine / 20 °C 2: triethylamine / CH2Cl2 / 0.25 h / 20 °C 3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane / 1.) dichloromethane, 30 min, 2.) dichloromethane, 60 min 4: 1.12 g / p-toluenesulfonic acid / CH2Cl2 / 0.03 h / 20 °C 5: 81 percent / silver oxide / acetone / 72 h / 20 °C 6: 75 percent / ammonia / tetrahydrofuran 7: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (69304-38-7) → 2'-O-methylcytidine (2140-72-9)

Conditions

Yield

Multi-step reaction with 6 steps 1: triethylamine / CH2Cl2 / 0.25 h / 20 °C 2: 1.) triethylamine, 2-mesitylenesulfonyl chloride, N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane / 1.) dichloromethane, 30 min, 2.) dichloromethane, 60 min 3: 1.12 g / p-toluenesulfonic acid / CH2Cl2 / 0.03 h / 20 °C 4: 81 percent / silver oxide / acetone / 72 h / 20 °C 5: 75 percent / ammonia / tetrahydrofuran 6: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

1,3,5-tri-O-benzoyl-2-O-methyl-α-D-ribofuranose (68045-07-8) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) HMDS, (NH4)2SO4, 2.) SnCl4 / 1.) reflux, overnight, 2.) dichloroethane, reflux, 60 min 2: 80 percent / NH3 / methanol / 48 h / 4 °C View Scheme

1,3,5-tri-O-benzoyl-α-D-ribofuranoside (22224-41-5) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 74 percent / BF3*(C2H5)2O / CH2Cl2 / 0 °C 2: 1.) HMDS, (NH4)2SO4, 2.) SnCl4 / 1.) reflux, overnight, 2.) dichloroethane, reflux, 60 min 3: 80 percent / NH3 / methanol / 48 h / 4 °C View Scheme

methanol-dichloromethane + CYTIDINE (65-46-3) + methyl iodide (74-88-4) → 2'-O-methylcytidine (2140-72-9)

Conditions	Yield
In N-methyl-acetamide; methanol; ethanol; dichloromethane

tert-butyldimethylsilyl chloride (18162-48-6) + 2'-O-methylcytidine (2140-72-9) → 5'-O-(tert-butyldimethylsilyl)-2'-O-methylcytidine (1171006-87-3)

Conditions	Yield
With pyridine at 20℃;	100%
With pyridine at 20℃;	100%
With pyridine at 20℃;

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) + 2'-O-methylcytidine (2140-72-9) → 3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methylcytidine (97626-19-2)

Conditions	Yield
With pyridine for 1h; Ambient temperature;	98%

tert-butyldimethylsilyl chloride (18162-48-6) + 2'-O-methylcytidine (2140-72-9) → 3',5'-O-bis(tert-butyldimethylsilyl)-2'-O-methylcytidine (367511-42-0)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 18h;	97.5%

2'-O-methylcytidine (2140-72-9) → 5-bromo-2'-O-methylcytidine (494210-77-4)

Conditions	Yield
With sodium azide; bromoisocyanuric acid monosodium salt In water; acetonitrile at 20℃; for 1.5h;	78%

trimethylsulphonium iodide (2181-42-2) + 2'-O-methylcytidine (2140-72-9) → 1-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-4-imino-3-methyl-3,4-dihydro-1H-pyrimidin-2-one (120057-51-4)

Conditions	Yield
In N,N-dimethyl-formamide at 85℃; for 3.5h; Rate constant; Product distribution; Mechanism; other nucleosides and trimethylsulphonium hydroxide;	67%
In N,N-dimethyl-formamide at 85℃; for 3.5h;	67%

(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester (1337529-56-2) + 2'-O-methylcytidine (2140-72-9) → C22H31N4O9P

Conditions	Yield
Stage #1: 2'-O-methylcytidine With isopropylmagnesium chloride In tetrahydrofuran at 0 - 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: (S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester In tetrahydrofuran at 0 - 20℃; Schlenk technique; Inert atmosphere;	16.3%

benzoic acid anhydride (93-97-0) + 2'-O-methylcytidine (2140-72-9) → 2'-O-methyl-N4-benzoylcytidine (52571-45-6)

Conditions	Yield
In ethanol for 1h; Heating;	0.38 g

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 2'-O-methylcytidine (2140-72-9) → 2'-O-methyl-4-N-(9-fluorenylmethoxycarbonyl)cytidine (135944-10-4)

Conditions	Yield
Yield given. Multistep reaction;

trimethylsulphonium hydroxide (17287-03-5) + 2'-O-methylcytidine (2140-72-9) → 1-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-4-imino-3-methyl-3,4-dihydro-1H-pyrimidin-2-one (120057-51-4) + N4,O2'-dimethylcytidine (13048-95-8) + O2',O3'-dimethyl-cytidine (34218-86-5)

Conditions	Yield
In methanol; N,N-dimethyl-formamide at 70℃; for 1h; Title compound not separated from byproducts;	A 34 % Spectr. B 21 % Spectr. C 8 % Spectr.

2'-O-methylcytidine (2140-72-9) → 5'-O-monomethoxytrityl 2'-O-methyl-N-benzoylcytidine (86872-24-4)

Conditions	Yield
Multistep reaction;

chloro-trimethyl-silane (75-77-4) + 2'-O-methylcytidine (2140-72-9) → 4-Amino-1-((2R,3R,4R,5R)-3-methoxy-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one

Conditions	Yield
In pyridine 0 deg C -> r.t. for 1-2 h;
With pyridine Silylation;

acetic anhydride (108-24-7) + 2'-O-methylcytidine (2140-72-9) → N4-acetyl-2'-O-methyl cytidine (113886-71-8)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; Acetylation;	0.94 g

2'-O-methylcytidine (2140-72-9) → 5-bromo-3'-O-[(tert-butyldimethyl)silyl]-2'-O-methylcytidine (444019-26-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97.5 percent / imidazole / dimethylformamide / 18 h / 20 °C 2: 83 percent / LiBr; ammonium ceric(IV) nitrate / acetonitrile / 3 h / 20 °C 3: 40 percent / aq. AcOH / 6 h / 50 °C View Scheme

2'-O-methylcytidine (2140-72-9) → 5-bromo-3',5'-O-bis[(tert-butyldimethyl)silyl]-2'-O-methylcytidine (848860-93-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 97.5 percent / imidazole / dimethylformamide / 18 h / 20 °C 2: 83 percent / LiBr; ammonium ceric(IV) nitrate / acetonitrile / 3 h / 20 °C View Scheme

2'-O-methylcytidine (2140-72-9) → N4-(4,4'-dimethoxytrityl)-2'-O-methylcytidine (444019-24-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97.5 percent / imidazole / dimethylformamide / 18 h / 20 °C 2: DMAP; pyridine / 20 °C 3: 1.8 g / triethylamine trihydrofluoride; triethylamine / tetrahydrofuran / 20 °C View Scheme

2'-O-methylcytidine (2140-72-9) → 2,2-dimethyl-thiopropionic acid S-(2-{[5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-4-methoxy-tetrahydro-furan-3-yloxy]-[2-(2,2-dimethyl-propionylsulfanyl)-ethoxy]-phosphoryloxy}-ethyl) ester

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 97.5 percent / imidazole / dimethylformamide / 18 h / 20 °C 2.1: DMAP; pyridine / 20 °C 3.1: 1.8 g / triethylamine trihydrofluoride; triethylamine / tetrahydrofuran / 20 °C 4.1: 1H-tetrazole / acetonitrile / 20 °C 4.2: 3-chloroperbenzoic acid / CH2Cl2 / 20 °C 4.3: aq. AcOH / methanol / 55 °C View Scheme

2'-O-methylcytidine (2140-72-9) → 2'-O-methylcytidine-5'-[bis-(S-pivaloyl-2-thioethyl)phosphate]

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 97.5 percent / imidazole / dimethylformamide / 18 h / 20 °C 2.1: DMAP; pyridine / 20 °C 3.1: 1.8 g / triethylamine trihydrofluoride; triethylamine / tetrahydrofuran / 20 °C 4.1: 1H-tetrazole / acetonitrile / 20 °C 4.2: 3-chloroperbenzoic acid / CH2Cl2 / 20 °C 4.3: 22 percent / aq. AcOH / methanol / 55 °C View Scheme

Upstream product

• 97626-19-2 3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methylcytidine 
• 73793-16-5 N⁴-benzoyl-3',5'-di-O-benzoyl-2'-O-methylcytidine 
• 186581-53-3 diazomethane 
• 65-46-3 CYTIDINE 
• 17287-03-5 trimethylsulphonium hydroxide 
• 1899-02-1 trimethylphenylammonium hydroxide 
• 74-88-4 methyl iodide 
• 121-43-7 Trimethyl borate 
• 10212-28-9 2,2'-anhydro-1-(β-D-arabinofuranosyl)cytosine acetate 
• 108782-90-7 1-(3',5'-O-1,1,3,3-tetraisopropyl-1,3-disilyl)-β-D-ribofuranosyl-4-(2-nitrophenyl)-2-pyrimidinone 
• 1085342-86-4 3',5'-di-O-acetyl-2'-O-methylcytidine 
• 2414-98-4 magnesium ethylate 
• 684-93-5 1-methyl-1-nitrosourea 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 

Downstream Products

• 113886-71-8 N⁴-acetyl-2'-O-methyl cytidine 
• 52571-45-6 2'-O-methyl-N⁴-benzoylcytidine 
• 110764-74-4 N⁴-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-methylcytidine 
• 444019-24-3 N⁴-(4,4'-dimethoxytrityl)-2'-O-methylcytidine 
• 86872-24-4 5'-O-monomethoxytrityl 2'-O-methyl-N-benzoylcytidine 
• 120057-51-4 1-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-4-imino-3-methyl-3,4-dihydro-1H-pyrimidin-2-one 
• 13048-95-8 N4,2'-O-dimethylcytidine 
• 34218-86-5 O^2'_,O3'-dimethyl-cytidine 

Relevant academic research and scientific papers

Efficient large scale synthesis of 2′-O-alkyl pyrimidine ribonucleosides

An efficient process to synthesize 2′-O-alkyl pyrimidine ribonucleosides in high yield has been described. The inexpensive method was used on a multikilogram-scale synthesis and optimized reaction conditions have been investigated.

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.

Synthesis and solution conformation studies of the modified nucleoside N4,2′-O-dimethylcytidine (m4Cm) and its analogues

The dimethylated ribosomal nucleoside m4Cm and its monomethylated analogues Cm and m4C were synthesized. The conformations (syn vs anti) of the three modified nucleosides and cytidine were determined by CD and 1D NOE difference spectroscopy. The ribose sugar puckers were determined by the use of proton coupling constants. The position of modification (e.g., O vs N methylation) was found to have an effect on the sugar pucker of cytidine.

Sugar modified oligonucleotides

Compositions and methods are provided for the treatment and diagnosis of diseases amenable to modulation of the production of selected proteins. In accordance with preferred embodiments, oligonucleotides and oligonucleotide analogs are provided which are specifically hybridizable with a selected sequence of RNA or DNA wherein at least one of the 2′-deoxyfuranosyl moieties of the nucleoside unit is modified. Treatment of diseases caused by various viruses and other causative agents is provided.

2'modified oligonucleotides

Compositions and methods are provided for the treatment and diagnosis of diseases amenable to modulation of the production of selected proteins. In accordance with preferred embodiments, oligonucleotides and oligonucleotide analogs are provided which are specifically hybridizable with a selected sequence of RNA or DNA wherein at least one of the 2′-deoxyfuranosyl moieties of the nucleoside unit is modified. Treatment of diseases caused by various viruses and other causative agents is provided.

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.

2'-modified oligonucleotides

Compositions and methods are provided for the treatment and diagnosis of diseases amenable to modulation of the production of selected proteins. In accordance with preferred embodiments, oligonucleotides and oligonucleotide analogs are provided which are specifically hybridizable with a selected sequence of RNA or DNA wherein at least one of the 2'-deoxyfuranosyl moieties of the nucleoside unit is modified. Treatment of diseases caused by various viruses and other causative agents is provided.

2'-O-modified oligonucleotides

Compositions and methods are provided for the treatment and diagnosis of diseases amenable to modulation of the production of selected proteins. In accordance with preferred embodiments, oligonucleotides and oligonucleotide analogs are provided which are specifically hybridizable with a selected sequence of RNA or DNA wherein at least one of the 2'-deoxyfuranosyl moieties of the nucleoside unit is modified. Treatment of diseases caused by various viruses and other causative agents is provided.

2'-modified oligonucleotides

Compositions and methods are provided for the treatment and diagnosis of diseases amenable to modulation of the production of selected proteins. In accordance with preferred embodiments, oligonucleotides and oligonucleotide analogs are provided which are specifically hybridizable with a selected sequence of RNA or DNA wherein at least one of the 2'-deoxyfuranosyl moieties of the nucleoside unit is modified. Treatment of diseases caused by various viruses and other causative agents is provided.

Chemical syntheses of 2'-O-methoxy purine nucleosides

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