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2140-76-3

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2140-76-3 Usage

Description

2'-O-Methyluridine is an analog of uridine and has been shown to have antiviral and anticancer properties. 2'-O-Methyluridine inhibits protein synthesis by competing with uridine for the active site of the enzyme ribonucleotide reductase, which converts ribonucleotides to dNMPs. This compound also inhibits RNA synthesis by disrupting the pairing of adenine and cytosine residues in RNA strands.

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 2140-76-3 differently. You can refer to the following data:
1. Uridine analog. 2'-O-Methyluridine is used for preparation of antiviral nucleoside derivatives as inhibitors of subgenomic hepatitis C virus RNA replication.
2. Uridine analog. Used for preparation of antiviral nucleoside derivatives as inhibitors of subgenomic hepatitis C virus RNA replication.

Definition

ChEBI: A methyluridine that consists of uridine bearing a single methyl substituent located at position O-2' on the ribose ring.

Check Digit Verification of cas no

The CAS Registry Mumber 2140-76-3 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 6 respectively.
Calculate Digit Verification of CAS Registry Number 2140-76:
(6*2)+(5*1)+(4*4)+(3*0)+(2*7)+(1*6)=53
53 % 10 = 3
So 2140-76-3 is a valid CAS Registry Number.

2140-76-3 Well-known Company Product Price

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  • TCI America

  • (M2290)  2'-O-Methyluridine  >98.0%(HPLC)(T)

  • 2140-76-3

  • 1g

  • 890.00CNY

  • Detail
  • TCI America

  • (M2290)  2'-O-Methyluridine  >98.0%(HPLC)(T)

  • 2140-76-3

  • 5g

  • 2,990.00CNY

  • Detail

2140-76-3SDS

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-methyluridine

1.2 Other means of identification

Product number -
Other names 2-O-Methyluridine

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:2140-76-3 SDS

2140-76-3Synthetic route

1'-(3',5'-O-benzyl-2'-O-methyl-β-D-ribofuranosyl)uracil
156541-83-2

1'-(3',5'-O-benzyl-2'-O-methyl-β-D-ribofuranosyl)uracil

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate at 25℃; under 760 Torr; for 0.5h;99%
3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disilyl)-2'-O-methyluridine
83167-64-0

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

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h;95%
With potassium fluoride; tetraethylammonium bromide In methanol; water78%
With potassium fluoride; tetraethylammonium chloride In water; acetonitrile at 53℃; for 0.5h;69 % Spectr.
With tetrabutyl ammonium fluoride In tetrahydrofuran
C25H28N2O7
1384271-34-4

C25H28N2O7

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
With formic acid; palladium on activated charcoal; hydrogen In water; isopropyl alcohol under 760.051 Torr; for 12h;95%
3',5'-O-1,1,3,3-tetraisopropyldisiloxyl-2'-O-methyl-3-N-(2,4-dinitrobenzene)sulfenyluridine
98917-55-6

3',5'-O-1,1,3,3-tetraisopropyldisiloxyl-2'-O-methyl-3-N-(2,4-dinitrobenzene)sulfenyluridine

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.0333333h;92%
2,2'-Anhydrouridine
3736-77-4

2,2'-Anhydrouridine

trimethyl orthoformate
149-73-5

trimethyl orthoformate

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
With Trimethyl borate; sodium carbonate In methanol at 140 - 150℃; Ring cleavage;92%
magnesium ethylate
2414-98-4

magnesium ethylate

O2,2'-anhydro-1-(β-D-arabinofuranosyl)uracil
292037-79-7

O2,2'-anhydro-1-(β-D-arabinofuranosyl)uracil

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
In methanol for 5h; Reflux; Large scale;92%
2,2'-Anhydrouridine
3736-77-4

2,2'-Anhydrouridine

magnesium methanolate
109-88-6, 16436-83-2, 16436-85-4

magnesium methanolate

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
In methanol for 5h; Heating;88%
3',5'-di-O-benzoyl-2'-O-methyluridine
79816-14-1

3',5'-di-O-benzoyl-2'-O-methyluridine

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
With ammonium hydroxide In methanol Ambient temperature;86%
Trimethyl borate
121-43-7

Trimethyl borate

1-((2R,4S,5R)-3,4-anhydro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-4(1H)-one
847650-91-3

1-((2R,4S,5R)-3,4-anhydro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-4(1H)-one

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
With sodium hydrogencarbonate; trimethyl orthoformate In methanol at 150℃; under 10343 Torr; for 42h;86%
2'-O-methyl-5'-O-(monomethoxytrityl)uridine
138935-28-1

2'-O-methyl-5'-O-(monomethoxytrityl)uridine

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
With acetic acid Ambient temperature;85%
3-(4-methoxyphenylmethyl)-2'-O-methyluridine
132278-69-4

3-(4-methoxyphenylmethyl)-2'-O-methyluridine

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
With aluminium trichloride; methoxybenzene at 65℃; for 2h;81%
2'-O-methyl-3-N-(2-nitrobenzene)sulfenyluridine
98889-58-8

2'-O-methyl-3-N-(2-nitrobenzene)sulfenyluridine

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
With triethylammonium thiocresolate In pyridine; acetonitrile for 0.166667h;81%
3',5'-O-1,1,3,3-tetraisopropyldisiloxyl-2'-O-methyl-3-N-(2-nitrobenzene)sulfenyluridine
98889-57-7

3',5'-O-1,1,3,3-tetraisopropyldisiloxyl-2'-O-methyl-3-N-(2-nitrobenzene)sulfenyluridine

A

2'-O-methyl-3-N-(2-nitrobenzene)sulfenyluridine
98889-58-8

2'-O-methyl-3-N-(2-nitrobenzene)sulfenyluridine

B

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.0333333h;A 81%
B 10%
1-((2R,3R,3aR,9aR)-3-Chloromethoxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidine-2,4-dione

1-((2R,3R,3aR,9aR)-3-Chloromethoxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidine-2,4-dione

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
Stage #1: 1-((2R,3R,3aR,9aR)-3-Chloromethoxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidine-2,4-dione With sodium tetrahydroborate In N,N-dimethyl-formamide
Stage #2: With potassium fluoride In tetrahydrofuran
18%
1-methyl-1-nitrosourea
684-93-5

1-methyl-1-nitrosourea

uridine
58-96-8

uridine

A

3-methyluridine
2140-69-4

3-methyluridine

B

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
With borax In water; formamide at 50℃; for 18h;A 11%
B n/a
uridine
58-96-8

uridine

A

3'-O-methyluridine
6038-59-1, 55062-69-6

3'-O-methyluridine

B

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
With tin(ll) chloride In N,N-dimethyl-formamide at 50℃; Title compound not separated from byproducts;
With tin(ll) chloride In N,N-dimethyl-formamide at 0℃; Title compound not separated from byproducts;
1-[6-methoxy-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro-[2,3-d][1,3]dioxol-5-yl]-(1R)-ethane-1,2-diol
18968-50-8, 29587-02-8, 32166-85-1, 36215-54-0, 43138-65-4, 65725-74-8, 67816-77-7

1-[6-methoxy-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro-[2,3-d][1,3]dioxol-5-yl]-(1R)-ethane-1,2-diol

1,3-bis(trimethylsilyl)uracil
3442-82-8

1,3-bis(trimethylsilyl)uracil

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
Multistep reaction;
3-N-(trimethylsilyl)ethoxymethyl-2'-O-methyluridine
174088-71-2

3-N-(trimethylsilyl)ethoxymethyl-2'-O-methyluridine

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran Heating;
3-N-(trimethylsilyl)ethoxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine
174088-69-8

3-N-(trimethylsilyl)ethoxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Af2O / 7 h / Heating
2: TBAF / tetrahydrofuran / 0.25 h / 0 °C
3: TBAF / tetrahydrofuran / Heating
View Scheme
3-N-(trimethylsilyl)ethoxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-methyluridine
174088-70-1

3-N-(trimethylsilyl)ethoxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-methyluridine

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TBAF / tetrahydrofuran / 0.25 h / 0 °C
2: TBAF / tetrahydrofuran / Heating
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-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 75 percent / i-Pr2NEt / CH2Cl2 / Ambient temperature
2: Af2O / 7 h / Heating
3: TBAF / tetrahydrofuran / 0.25 h / 0 °C
4: TBAF / tetrahydrofuran / Heating
View Scheme
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: 70 percent / syn-4-nitrobenxaldoxime, N1,N1,N3,N3-tetramethylguanidine / dioxane; H2O / 16 h / 20 °C
6: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: 87 percent / pyridine / 0 °C
2: 83 percent / pyridine / Ambient temperature
3: 77 percent / t-butylamine / methanol / 0.33 h / Ambient temperature
4: 93 percent / Ag2O / 7 h / Ambient temperature
5: 86 percent / zinc powder, acetylacetone / pyridine / 0.25 h / Ambient temperature
6: 69 percent Spectr. / potassium fluoride, tetraethylammonium chloride / acetonitrile; H2O / 0.5 h / 53 °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-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0.5 h / Ambient temperature
2: 86 percent / conc. aq. NH4OH / methanol / Ambient temperature
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-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 71 percent / CH2N2, BF3*OEt2 / CH2Cl2 / 0.5 h / 4 °C
2: 75 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0.5 h / Ambient temperature
3: 86 percent / conc. aq. NH4OH / methanol / Ambient temperature
View Scheme
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-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 81 percent / silver oxide / acetone / 72 h / 20 °C
2: 70 percent / syn-4-nitrobenxaldoxime, N1,N1,N3,N3-tetramethylguanidine / dioxane; H2O / 16 h / 20 °C
3: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 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-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / syn-4-nitrobenxaldoxime, N1,N1,N3,N3-tetramethylguanidine / dioxane; H2O / 16 h / 20 °C
2: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 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-methyluridine
2140-76-3

2'-O-methyluridine

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: 70 percent / syn-4-nitrobenxaldoxime, N1,N1,N3,N3-tetramethylguanidine / dioxane; H2O / 16 h / 20 °C
4: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 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-methyluridine
2140-76-3

2'-O-methyluridine

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: 70 percent / syn-4-nitrobenxaldoxime, N1,N1,N3,N3-tetramethylguanidine / dioxane; H2O / 16 h / 20 °C
5: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
uridine
58-96-8

uridine

aqueous H3PO4

aqueous H3PO4

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

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: 70 percent / syn-4-nitrobenxaldoxime, N1,N1,N3,N3-tetramethylguanidine / dioxane; H2O / 16 h / 20 °C
7: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
2: Ag2O / acetone / 16 h / 20 °C
3: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
2: 94 percent / Ag2O / acetone / 16 h / 20 °C
3: 81 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h / 20 °C
4: 81 percent / triethylammonium thiocresolate / pyridine; acetonitrile / 0.17 h
View Scheme
Multi-step reaction with 3 steps
2: 94 percent / Ag2O / acetone / 16 h / 20 °C
3: 10 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h / 20 °C
View Scheme
N3-<(2-nitrophenyl)sulfenyl>-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine
98889-55-5

N3-<(2-nitrophenyl)sulfenyl>-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 94 percent / Ag2O / acetone / 16 h / 20 °C
2: 81 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h / 20 °C
3: 81 percent / triethylammonium thiocresolate / pyridine; acetonitrile / 0.17 h
View Scheme
Multi-step reaction with 2 steps
1: 94 percent / Ag2O / acetone / 16 h / 20 °C
2: 10 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h / 20 °C
View Scheme
acetic anhydride
108-24-7

acetic anhydride

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

3',5'-di-O-acetyl-2'-O-methyluridine
61671-79-2

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

Conditions
ConditionsYield
With pyridine Acetylation;100%
With pyridine; dmap at 20℃;95%
With pyridine at 20℃; for 6h; Acetylation;93%
With pyridine at 20℃; for 18h;
In pyridine at 20℃; for 18h;
tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

3'-O-(tert-butyldiphenylsilyl)-2'-O-methyluridine

3'-O-(tert-butyldiphenylsilyl)-2'-O-methyluridine

Conditions
ConditionsYield
Stage #1: 2'-O-methyluridine With pyridine; tert-butyldimethylsilyl chloride at 20℃; for 12h;
Stage #2: tert-butylchlorodiphenylsilane With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 12h;
Stage #3: With toluene-4-sulfonic acid In methanol at 20℃; for 3h;
93%
2'-O-methyluridine
2140-76-3

2'-O-methyluridine

5-bromo-2'-O-methyluridine
34218-83-2

5-bromo-2'-O-methyluridine

Conditions
ConditionsYield
With sodium azide; bromoisocyanuric acid monosodium salt In water; acetonitrile at 20℃; for 1.5h;93%
Stage #1: 2'-O-methyluridine With sodium azide In 1,2-dimethoxyethane; water at 22℃; for 0.25h; Inert atmosphere;
Stage #2: With N-Bromosuccinimide In 1,2-dimethoxyethane; water at 22℃; for 24h; Inert atmosphere;
88%
2'-O-methyluridine
2140-76-3

2'-O-methyluridine

O-levulinyl acetonoxime
647834-80-8

O-levulinyl acetonoxime

5’-O-levulinoyl-2’-O-methyluridine
1417910-03-2

5’-O-levulinoyl-2’-O-methyluridine

Conditions
ConditionsYield
With Candida antarctica lipase B In tetrahydrofuran at 30℃; for 1h; Inert atmosphere; Enzymatic reaction; regioselective reaction;92%
2'-O-methyluridine
2140-76-3

2'-O-methyluridine

5′-iodo-2′-deoxy-2′-methoxyuridine

5′-iodo-2′-deoxy-2′-methoxyuridine

Conditions
ConditionsYield
With iodine; triphenylphosphine In pyridine; acetonitrile at 20℃; for 48h; Inert atmosphere;91%
With 1H-imidazole; iodine; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 3h;86%
With 1H-imidazole; iodine; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 3h;86%
4,4'-dimethoxytrityl chloride
40615-36-9

4,4'-dimethoxytrityl chloride

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

5'-O-(4,4'-dimethoxytrityl)-2'-O-methyluridine
103285-22-9

5'-O-(4,4'-dimethoxytrityl)-2'-O-methyluridine

Conditions
ConditionsYield
With pyridine for 0.75h; Inert atmosphere;90%
With pyridine at 0 - 20℃;
2'-O-methyluridine
2140-76-3

2'-O-methyluridine

1-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-tetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1H,3H)-dione
34218-84-3

1-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-tetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate; iodine In acetonitrile at 80℃; for 1h;86%
With ammonium cerium(IV) nitrate; iodine; acetic acid at 80℃;74%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

C22H42N2O6Si2
367511-37-3

C22H42N2O6Si2

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h;85%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h;85%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h;85%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h;85%
With 1H-imidazole In N,N-dimethyl-formamide
succinic acid anhydride
108-30-5

succinic acid anhydride

4,4'-dimethoxytrityl chloride
40615-36-9

4,4'-dimethoxytrityl chloride

triethylamine
121-44-8

triethylamine

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

2'-O-methyl-3'-O-succinyl-5′-O-(4'',4'''-dimethoxytriphenylmethyl)uridine triethylammonium salt

2'-O-methyl-3'-O-succinyl-5′-O-(4'',4'''-dimethoxytriphenylmethyl)uridine triethylammonium salt

Conditions
ConditionsYield
Stage #1: 4,4'-dimethoxytrityl chloride; triethylamine; 2'-O-methyluridine In N,N-dimethyl-formamide for 2h;
Stage #2: succinic acid anhydride With 1-methyl-1H-imidazole In N,N-dimethyl-formamide
83.9%
benzyl bromide
100-39-0

benzyl bromide

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

3-benzyl-2'-O-methyluridine

3-benzyl-2'-O-methyluridine

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide for 3h; Heating;75%
2'-O-methyluridine
2140-76-3

2'-O-methyluridine

C10H13BrN2O5

C10H13BrN2O5

Conditions
ConditionsYield
With carbon tetrabromide; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 4h;71%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

2'-O-methyl-5'-O-p-tolylsulfonyluridine
175471-63-3

2'-O-methyl-5'-O-p-tolylsulfonyluridine

Conditions
ConditionsYield
In pyridine Ambient temperature; overnight;60%
2,7-dimethyl-9-(4-nitrophenyl)-xanthen-9-ol
1392228-32-8

2,7-dimethyl-9-(4-nitrophenyl)-xanthen-9-ol

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

5'-O-DMPx-2-O-Me-uridine
1411689-69-4

5'-O-DMPx-2-O-Me-uridine

Conditions
ConditionsYield
Stage #1: 2'-O-methyluridine With tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 0.5h;
Stage #2: 2,7-dimethyl-9-(4-nitrophenyl)-xanthen-9-ol In dichloromethane at 20℃; for 3h; Inert atmosphere; regioselective reaction;
60%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

C11H16N2O8S
1613530-35-0

C11H16N2O8S

Conditions
ConditionsYield
With pyridine at -78 - 20℃; for 1h;50%
With pyridine at -78 - 20℃; for 1h;50%
With pyridine at -78 - 20℃; for 1h;50%
With pyridine at -78 - 20℃; for 1h;50%
2'-O-methyluridine
2140-76-3

2'-O-methyluridine

C10H12N2O7
1558010-48-2

C10H12N2O7

Conditions
ConditionsYield
With dipotassium peroxodisulfate; ruthenium(III) chloride trihydrate; potassium hydroxide In water at 25℃;41%
pyrrolidine
123-75-1

pyrrolidine

formaldehyd
50-00-0

formaldehyd

2'-O-methyluridine
2140-76-3

2'-O-methyluridine

C15H23N3O6
1613530-47-4

C15H23N3O6

Conditions
ConditionsYield
In water at 105℃; for 48h;32%
In water at 105℃; for 48h;32%
In water at 105℃; for 48h;32%
In water at 105℃; for 48h;32%

2140-76-3Relevant articles and documents

A novel and economical synthesis of 2′-o-alkyl-uridines

Ross, Bruce S.,Springer, Robert H.,Tortorici, Zeb,Dimock, Stuart

, p. 1641 - 1643 (1997)

A highly efficient, two-step method to make 2′-O-methyluridine is described using only inexpensive reagents and no chromatography. The method is applicable for some other alkyls as well as some other pyrimidine derivatives. Copyright

SYNTHESIS AND STRUCTURE OF HIGH POTENCY RNA THERAPEUTICS

-

, (2019/01/15)

This invention provides expressible polynucleotides, which can express a target protein or polypeptide. Synthetic mRNA constructs for producing a protein or polypeptide can contain one or more 5′ UTRs, where a 5′ UTR may be expressed by a gene of a plant. In some embodiments, a 5′ UTR may be expressed by a gene of a member of Arabidopsis genus. The synthetic mRNA constructs can be used as pharmaceutical agents for expressing a target protein or polypeptide in vivo.

Regioselective Mitsunobu Reaction of Partially Protected Uridine

Szlenkier, Maurycy,Kamel, Karol,Boryski, Jerzy

, p. 410 - 425 (2016/08/05)

Mitsunobu reaction of partially acylated uridine proceeds with high regioselectivity for intramolecular SN2 anhydro linkage closuring. Under the reaction conditions, an isomeric mixture of diacyl uridine derivatives with either free 2′- or 3′-hydroxyl group was transformed into a single cyclonucleosidic product, 2,2′-anhydro-3′,5′-di-O-acyluridine. This paper presents a possible mechanism of the reactions, the explanation of observed phenomenon based on semiempirical and density functional theory (DFT) calculations and possible utility of this synthetic pathway.

Synthesis and hybridization properties of 2′-O-methylated oligoribonucleotides incorporating 2′-O-naphthyluridines

Sekine, Mitsuo,Oeda, Yusuke,Iijima, Yoshihiro,Taguchi, Haruhiko,Ohkubo, Akihiro,Seio, Kohji

experimental part, p. 210 - 218 (2011/02/23)

2′-O-(1-Naphthyl)uridine and 2′-O-(2-naphthyl)uridine were synthesized by a microwave-mediated reaction of 2,2′-anhydrouridine with naphthols. Using the 3′-phosphoramidite building blocks, these 2′-O-aryluridine derivatives were incorporated into 2′-O-methylated oligoribonucleotides. Incorporation of five 2′-O-(2-naphthyl)uridines into a 2′-O-methylated RNA sense strand significantly increased the thermostability of the duplex with a 2′-O-methylated RNA antisense strand. Circular dichroism spectroscopy and molecular dynamic simulation of the duplexes formed between the modified RNAs and 2′-O-methyl RNAs suggested that there are π-π interactions between two neighboring naphthyl groups in a sequence of the five consecutively modified nucleosides.

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