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3',5'-di-O-acetyl-2'-O-methylcytidine
2'-O-methylcytidine
Conditions | Yield |
---|---|
With ammonia In methanol at 20℃; | 99% |
3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methylcytidine
2'-O-methylcytidine
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; | 96% |
N4-benzoyl-3',5'-di-O-benzoyl-2'-O-methylcytidine
2'-O-methylcytidine
Conditions | Yield |
---|---|
With ammonia In methanol at 4℃; for 48h; | 80% |
Conditions | Yield |
---|---|
In methanol for 5h; Reflux; | 76% |
diazomethane
CYTIDINE
A
3'-O-Methylcytidine
B
2'-O-methylcytidine
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
CYTIDINE
A
3'-O-Methylcytidine
B
2'-O-methylcytidine
C
N3-methylcytidine
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
CYTIDINE
A
3'-O-Methylcytidine
B
2'-O-methylcytidine
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
CYTIDINE
A
3-methyluridine
B
3'-O-Methylcytidine
C
2'-O-methylcytidine
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
CYTIDINE
A
2'-O-methylcytidine
B
N3-methylcytidine
Conditions | Yield |
---|---|
With borax In water; formamide at 50℃; for 18h; | A 5% B n/a |
CYTIDINE
methyl iodide
A
3'-O-Methylcytidine
B
2'-O-methylcytidine
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; |
2'-O-methylcytidine
Conditions | Yield |
---|---|
With dichloro-acetic acid; ammonium hydroxide |
Trimethyl borate
2,2'-anhydro-1-(β-D-arabinofuranosyl)cytosine acetate
2'-O-methylcytidine
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
2'-O-methylcytidine
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
2'-O-methylcytidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 75 percent / ammonia / tetrahydrofuran 2: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C View Scheme |
2'-O-methylcytidine
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
2'-O-methylcytidine
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 |
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
2'-O-methylcytidine
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
2'-O-methylcytidine
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
2'-O-methylcytidine
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 |
Conditions | Yield |
---|---|
In N-methyl-acetamide; methanol; ethanol; dichloromethane |
tert-butyldimethylsilyl chloride
2'-O-methylcytidine
5'-O-(tert-butyldimethylsilyl)-2'-O-methylcytidine
Conditions | Yield |
---|---|
With pyridine at 20℃; | 100% |
With pyridine at 20℃; | 100% |
With pyridine at 20℃; |
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane
2'-O-methylcytidine
3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methylcytidine
Conditions | Yield |
---|---|
With pyridine for 1h; Ambient temperature; | 98% |
tert-butyldimethylsilyl chloride
2'-O-methylcytidine
3',5'-O-bis(tert-butyldimethylsilyl)-2'-O-methylcytidine
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 18h; | 97.5% |
2'-O-methylcytidine
5-bromo-2'-O-methylcytidine
Conditions | Yield |
---|---|
With sodium azide; bromoisocyanuric acid monosodium salt In water; acetonitrile at 20℃; for 1.5h; | 78% |
trimethylsulphonium iodide
2'-O-methylcytidine
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
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
2'-O-methylcytidine
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
2'-O-methylcytidine
2'-O-methyl-N4-benzoylcytidine
Conditions | Yield |
---|---|
In ethanol for 1h; Heating; | 0.38 g |
(fluorenylmethoxy)carbonyl chloride
2'-O-methylcytidine
2'-O-methyl-4-N-(9-fluorenylmethoxycarbonyl)cytidine
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
trimethylsulphonium hydroxide
2'-O-methylcytidine
A
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
B
N4,O2'-dimethylcytidine
C
O2',O3'-dimethyl-cytidine
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
5'-O-monomethoxytrityl 2'-O-methyl-N-benzoylcytidine
Conditions | Yield |
---|---|
Multistep reaction; |
Conditions | Yield |
---|---|
In pyridine 0 deg C -> r.t. for 1-2 h; | |
With pyridine Silylation; |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; Acetylation; | 0.94 g |
2'-O-methylcytidine
5-bromo-3'-O-[(tert-butyldimethyl)silyl]-2'-O-methylcytidine
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
5-bromo-3',5'-O-bis[(tert-butyldimethyl)silyl]-2'-O-methylcytidine
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
N4-(4,4'-dimethoxytrityl)-2'-O-methylcytidine
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
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
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 |
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