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2140-72-9

Basic Information
CAS No.: 2140-72-9
Name: Cytidine, 2'-O-methyl-
Molecular Structure:
Molecular Structure of 2140-72-9 (Cytidine, 2'-O-methyl-)
Formula: C10H15N3O5
Molecular Weight: 257.24
Synonyms: O2'-Methylcytidine;2'-OMe-C;
EINECS: 2017-001-1
Density: 1.68 g/cm3
Melting Point: 252-253 °C
Boiling Point: 506 °C at 760 mmHg
Flash Point: 259.8 °C
Solubility:
Appearance:
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information:
PSA: 119.83000
LogP: -1.32770
Synthetic route
1085342-86-4

3',5'-di-O-acetyl-2'-O-methylcytidine

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
With ammonia In methanol at 20℃;99%
97626-19-2

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methylcytidine

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;96%
73793-16-5

N4-benzoyl-3',5'-di-O-benzoyl-2'-O-methylcytidine

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
With ammonia In methanol at 4℃; for 48h;80%
2414-98-4

magnesium ethylate

2,2'-anhydrocytidine hydrochloride

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
In methanol for 5h; Reflux;76%
65-46-3

CYTIDINE

A

20594-00-7

3'-O-Methylcytidine

B

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
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
17287-03-5

trimethylsulphonium hydroxide

65-46-3

CYTIDINE

A

20594-00-7

3'-O-Methylcytidine

B

2140-72-9

2'-O-methylcytidine

C

2140-64-9

N3-methylcytidine

Conditions
ConditionsYield
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.
17287-03-5

trimethylsulphonium hydroxide

65-46-3

CYTIDINE

A

20594-00-7

3'-O-Methylcytidine

B

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
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%
1899-02-1

trimethylphenylammonium hydroxide

65-46-3

CYTIDINE

A

2140-69-4

3-methyluridine

B

20594-00-7

3'-O-Methylcytidine

C

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
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%
684-93-5

1-methyl-1-nitrosourea

65-46-3

CYTIDINE

A

2140-72-9

2'-O-methylcytidine

B

2140-64-9

N3-methylcytidine

Conditions
ConditionsYield
With borax In water; formamide at 50℃; for 18h;A 5%
B n/a
65-46-3

CYTIDINE

74-88-4

methyl iodide

A

20594-00-7

3'-O-Methylcytidine

B

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
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

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
With dichloro-acetic acid; ammonium hydroxide
121-43-7

Trimethyl borate

10212-28-9

2,2'-anhydro-1-(β-D-arabinofuranosyl)cytosine acetate

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
With methanol; boron trifluoride for 48h; Ring cleavage; Heating;
108782-90-7

1-(3',5'-O-1,1,3,3-tetraisopropyl-1,3-disilyl)-β-D-ribofuranosyl-4-(2-nitrophenyl)-2-pyrimidinone

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
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
110567-19-6

1-(3',5'-O-1,1,3,3-tetraisopropyl-1,3-disilyl)-β-D-ribofuranosyl-2'-O-methyl-4-(2-nitrophenyl)-2-pyrimidinone

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
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

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
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
415903-48-9

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-2'-O-(trimethylsilyl)uridine

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
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
58-96-8

uridine

aqueous H3PO4

aqueous H3PO4

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
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
69304-38-7

3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
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
68045-07-8

1,3,5-tri-O-benzoyl-2-O-methyl-α-D-ribofuranose

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
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
22224-41-5

1,3,5-tri-O-benzoyl-α-D-ribofuranoside

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
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

65-46-3

CYTIDINE

74-88-4

methyl iodide

2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
In N-methyl-acetamide; methanol; ethanol; dichloromethane
18162-48-6

tert-butyldimethylsilyl chloride

2140-72-9

2'-O-methylcytidine

1171006-87-3

5'-O-(tert-butyldimethylsilyl)-2'-O-methylcytidine

Conditions
ConditionsYield
With pyridine at 20℃;100%
With pyridine at 20℃;100%
With pyridine at 20℃;
69304-37-6

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

2140-72-9

2'-O-methylcytidine

97626-19-2

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methylcytidine

Conditions
ConditionsYield
With pyridine for 1h; Ambient temperature;98%
18162-48-6

tert-butyldimethylsilyl chloride

2140-72-9

2'-O-methylcytidine

367511-42-0

3',5'-O-bis(tert-butyldimethylsilyl)-2'-O-methylcytidine

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 18h;97.5%
2140-72-9

2'-O-methylcytidine

494210-77-4

5-bromo-2'-O-methylcytidine

Conditions
ConditionsYield
With sodium azide; bromoisocyanuric acid monosodium salt In water; acetonitrile at 20℃; for 1.5h;78%
2181-42-2

trimethylsulphonium iodide

2140-72-9

2'-O-methylcytidine

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

Conditions
ConditionsYield
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%
1337529-56-2

(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester

2140-72-9

2'-O-methylcytidine

C22H31N4O9P

Conditions
ConditionsYield
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%
93-97-0

benzoic acid anhydride

2140-72-9

2'-O-methylcytidine

52571-45-6

2'-O-methyl-N4-benzoylcytidine

Conditions
ConditionsYield
In ethanol for 1h; Heating;0.38 g
28920-43-6

(fluorenylmethoxy)carbonyl chloride

2140-72-9

2'-O-methylcytidine

135944-10-4

2'-O-methyl-4-N-(9-fluorenylmethoxycarbonyl)cytidine

Conditions
ConditionsYield
Yield given. Multistep reaction;
17287-03-5

trimethylsulphonium hydroxide

2140-72-9

2'-O-methylcytidine

A

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

B

13048-95-8

N4,O2'-dimethylcytidine

C

34218-86-5

O2',O3'-dimethyl-cytidine

Conditions
ConditionsYield
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.
2140-72-9

2'-O-methylcytidine

86872-24-4

5'-O-monomethoxytrityl 2'-O-methyl-N-benzoylcytidine

Conditions
ConditionsYield
Multistep reaction;
75-77-4

chloro-trimethyl-silane

2140-72-9

2'-O-methylcytidine

4-Amino-1-((2R,3R,4R,5R)-3-methoxy-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one

Conditions
ConditionsYield
In pyridine 0 deg C -> r.t. for 1-2 h;
With pyridine Silylation;
108-24-7

acetic anhydride

2140-72-9

2'-O-methylcytidine

113886-71-8

N4-acetyl-2'-O-methyl cytidine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; Acetylation;0.94 g
2140-72-9

2'-O-methylcytidine

444019-26-5

5-bromo-3'-O-[(tert-butyldimethyl)silyl]-2'-O-methylcytidine

Conditions
ConditionsYield
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
2140-72-9

2'-O-methylcytidine

848860-93-5

5-bromo-3',5'-O-bis[(tert-butyldimethyl)silyl]-2'-O-methylcytidine

Conditions
ConditionsYield
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
2140-72-9

2'-O-methylcytidine

444019-24-3

N4-(4,4'-dimethoxytrityl)-2'-O-methylcytidine

Conditions
ConditionsYield
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
2140-72-9

2'-O-methylcytidine

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
ConditionsYield
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
2140-72-9

2'-O-methylcytidine

2'-O-methylcytidine-5'-[bis-(S-pivaloyl-2-thioethyl)phosphate]

Conditions
ConditionsYield
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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    2'-O-Methylcytidine

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    2'-O-Methylcytidine

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Specification

The Cytidine, 2'-O-methyl-, with CAS registry number 2140-72-9, belongs to the following product categories: (1)Biochemicals and Reagents; (2)Nucleoside Analogs; (3)Nucleosides, Nucleotides, Oligonucleotides. It has the systematic name of 2'-O-methylcytidine. This chemical should be stored at the temperature of −20°C. And the chemical formula of this chemical is C10H15N3O5.

Physical properties of Cytidine, 2'-O-methyl-: (1)ACD/LogP: -1.09; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.09; (4)ACD/LogD (pH 7.4): -1.09; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 6.07; (8)ACD/KOC (pH 7.4): 6.1; (9)#H bond acceptors: 8; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 72.83 Å2; (13)Index of Refraction: 1.677; (14)Molar Refractivity: 57.6 cm3; (15)Molar Volume: 152.8 cm3; (16)Polarizability: 22.83×10-24cm3; (17)Surface Tension: 68.4 dyne/cm; (18)Density: 1.68 g/cm3; (19)Flash Point: 259.8 °C; (20)Enthalpy of Vaporization: 89.33 kJ/mol; (21)Boiling Point: 506 °C at 760 mmHg; (22)Vapour Pressure: 2.33E-12 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
The Cytidine, 2'-O-methyl- irritates to eyes, respiratory system and skin. When use it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1/N=C(/N)\C=C/N1[C@@H]2O[C@@H]([C@@H](O)[C@H]2OC)CO
(2)InChI: InChI=1/C10H15N3O5/c1-17-8-7(15)5(4-14)18-9(8)13-3-2-6(11)12-10(13)16/h2-3,5,7-9,14-15H,4H2,1H3,(H2,11,12,16)/t5-,7-,8-,9-/m1/s1
(3)InChIKey: RFCQJGFZUQFYRF-ZOQUXTDFBZ
(4)Std. InChI: InChI=1S/C10H15N3O5/c1-17-8-7(15)5(4-14)18-9(8)13-3-2-6(11)12-10(13)16/h2-3,5,7-9,14-15H,4H2,1H3,(H2,11,12,16)/t5-,7-,8-,9-/m1/s1
(5)Std. InChIKey: RFCQJGFZUQFYRF-ZOQUXTDFSA-N