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2140-72-9

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2140-72-9 Usage

Description

2'-O-Methylcytidine is a cytidine analog that is modified with a methyl group at the 2' position of the ribose sugar. It is a white powder and is used in the preparation of nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 2140-72-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,4 and 0 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 2140-72:
(6*2)+(5*1)+(4*4)+(3*0)+(2*7)+(1*2)=49
49 % 10 = 9
So 2140-72-9 is a valid CAS Registry Number.

2140-72-9 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (M2317)  2'-O-Methylcytidine  >98.0%(HPLC)(T)

  • 2140-72-9

  • 200mg

  • 480.00CNY

  • Detail
  • TCI America

  • (M2317)  2'-O-Methylcytidine  >98.0%(HPLC)(T)

  • 2140-72-9

  • 1g

  • 1,290.00CNY

  • Detail

2140-72-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2'-O-methylcytidine

1.2 Other means of identification

Product number -
Other names 2'-OMe Cytidine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2140-72-9 SDS

2140-72-9Synthetic route

3',5'-di-O-acetyl-2'-O-methylcytidine
1085342-86-4

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

2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
With ammonia In methanol at 20℃;99%
3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methylcytidine
97626-19-2

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

2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;96%
N4-benzoyl-3',5'-di-O-benzoyl-2'-O-methylcytidine
73793-16-5

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

2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

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

magnesium ethylate

2,2'-anhydrocytidine hydrochloride

2,2'-anhydrocytidine hydrochloride

2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

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

CYTIDINE

A

3'-O-Methylcytidine
20594-00-7

3'-O-Methylcytidine

B

2'-O-methylcytidine
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
trimethylsulphonium hydroxide
17287-03-5

trimethylsulphonium hydroxide

CYTIDINE
65-46-3

CYTIDINE

A

3'-O-Methylcytidine
20594-00-7

3'-O-Methylcytidine

B

2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

C

N3-methylcytidine
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.
trimethylsulphonium hydroxide
17287-03-5

trimethylsulphonium hydroxide

CYTIDINE
65-46-3

CYTIDINE

A

3'-O-Methylcytidine
20594-00-7

3'-O-Methylcytidine

B

2'-O-methylcytidine
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%
trimethylphenylammonium hydroxide
1899-02-1

trimethylphenylammonium hydroxide

CYTIDINE
65-46-3

CYTIDINE

A

3-methyluridine
2140-69-4

3-methyluridine

B

3'-O-Methylcytidine
20594-00-7

3'-O-Methylcytidine

C

2'-O-methylcytidine
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%
1-methyl-1-nitrosourea
684-93-5

1-methyl-1-nitrosourea

CYTIDINE
65-46-3

CYTIDINE

A

2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

B

N3-methylcytidine
2140-64-9

N3-methylcytidine

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

CYTIDINE

methyl iodide
74-88-4

methyl iodide

A

3'-O-Methylcytidine
20594-00-7

3'-O-Methylcytidine

B

2'-O-methylcytidine
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

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

2'-O-methylcytidine

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

Trimethyl borate

2,2'-anhydro-1-(β-D-arabinofuranosyl)cytosine acetate
10212-28-9

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

2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

Conditions
ConditionsYield
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

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

2'-O-methylcytidine
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
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

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
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

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

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

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

2'-O-methylcytidine
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
uridine
58-96-8

uridine

aqueous H3PO4

aqueous H3PO4

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

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

2'-O-methylcytidine
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
1,3,5-tri-O-benzoyl-2-O-methyl-α-D-ribofuranose
68045-07-8

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

2'-O-methylcytidine
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
1,3,5-tri-O-benzoyl-α-D-ribofuranoside
22224-41-5

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

2'-O-methylcytidine
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

methanol-dichloromethane

CYTIDINE
65-46-3

CYTIDINE

methyl iodide
74-88-4

methyl iodide

2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

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

tert-butyldimethylsilyl chloride

2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

5'-O-(tert-butyldimethylsilyl)-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℃;
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane
69304-37-6

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

2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-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%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

3',5'-O-bis(tert-butyldimethylsilyl)-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%
2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

5-bromo-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%
trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

2'-O-methylcytidine
2140-72-9

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
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%
(S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester
1337529-56-2

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

2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

C22H31N4O9P

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%
benzoic acid anhydride
93-97-0

benzoic acid anhydride

2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

2'-O-methyl-N4-benzoylcytidine
52571-45-6

2'-O-methyl-N4-benzoylcytidine

Conditions
ConditionsYield
In ethanol for 1h; Heating;0.38 g
(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

2'-O-methyl-4-N-(9-fluorenylmethoxycarbonyl)cytidine
135944-10-4

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

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

trimethylsulphonium hydroxide

2'-O-methylcytidine
2140-72-9

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
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

N4,O2'-dimethylcytidine
13048-95-8

N4,O2'-dimethylcytidine

C

O2',O3'-dimethyl-cytidine
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.
2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

5'-O-monomethoxytrityl 2'-O-methyl-N-benzoylcytidine
86872-24-4

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

Conditions
ConditionsYield
Multistep reaction;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

2'-O-methylcytidine
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

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;
acetic anhydride
108-24-7

acetic anhydride

2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

N4-acetyl-2'-O-methyl cytidine
113886-71-8

N4-acetyl-2'-O-methyl cytidine

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

2'-O-methylcytidine

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

2'-O-methylcytidine

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

2'-O-methylcytidine

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

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
2'-O-methylcytidine
2140-72-9

2'-O-methylcytidine

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

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

2140-72-9Relevant articles and documents

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

Roy, Saroj K.,Tang, Jin-Yan

, p. 170 - 171 (2000)

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.

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Hingerty et al.

, p. 1349 (1977)

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Hudson et al.

, p. 2009 (1965)

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

Mahto, Santosh K.,Chow, Christine S.

, p. 8795 - 8800 (2008/12/23)

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.

2'modified oligonucleotides

-

, (2008/06/13)

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.

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