e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Biochemistry

Chemical synthesis of LNA-2-thiouridine and its influence on stability and selectivity of oligonucleotide binding to RNA

M Carlucci, E Kierzek, A Olejnik, DH Turner…

Index: Okamoto, Itaru; Shohda, Koh-Ichiroh; Seio, Kohji; Sekine, Mitsuo Journal of Organic Chemistry, 2003 , vol. 68, # 26 p. 9971 - 9982

Full Text: HTML

Citation Number: 12

Abstract

... Select a Journal or Book ... Oligonucleotides were synthesized on an Applied Biosystems DNA/RNA synthesizer, using β-cyanoethyl phosphoramidite chemistry (29). ... The organic layers were combined, dried with anhydrous sodium sulfate, and evaporated to heavy oil. ...

2'-O-allyl-4-O-(2,6-dimethylphenyl)-2-thiouridine Structure

2'-O-allyl-4-O-...

~77%

1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-prop-2-enoxyoxolan-2-yl]-2-sulfanylidenepyrimidin-4-one Structure

1-[(2R,3R,4R,5R...

3',5'-O-(1,1,3,3-TETRAISOPROPYL-1,3-DISILOXANEDIYL)URIDINE Structure

3',5'-O-(1,1,3,...

~%

1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-prop-2-enoxyoxolan-2-yl]-2-sulfanylidenepyrimidin-4-one Structure

1-[(2R,3R,4R,5R...

4-O-(2,6-dimethylphenyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine Structure

4-O-(2,6-dimeth...

~%

1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-prop-2-enoxyoxolan-2-yl]-2-sulfanylidenepyrimidin-4-one Structure

1-[(2R,3R,4R,5R...

2'-O-allyl-4-O-(2,6-dimethylphenyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine Structure

2'-O-allyl-4-O-...

~%

1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-prop-2-enoxyoxolan-2-yl]-2-sulfanylidenepyrimidin-4-one Structure

1-[(2R,3R,4R,5R...

2'-O-allyl-4-O-(2,6-dimethylphenyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-thiouridine Structure

2'-O-allyl-4-O-...

~%

1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-prop-2-enoxyoxolan-2-yl]-2-sulfanylidenepyrimidin-4-one Structure

1-[(2R,3R,4R,5R...

2-(((6aR,8R,9R,9aR)-2,2,4,4-tetraisopropyl-8-(4-oxo-2-thioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl)oxy)ethyl acetate Structure

2-(((6aR,8R,9R,...

~98%

2-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-(4-oxo-2-sulfanylidenepyrimidin-1-yl)oxolan-3-yl]oxyethyl acetate Structure

2-[(2R,3R,4R,5R...

3',5'-O-(1,1,3,3-TETRAISOPROPYL-1,3-DISILOXANEDIYL)URIDINE Structure

3',5'-O-(1,1,3,...

~%

2-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-(4-oxo-2-sulfanylidenepyrimidin-1-yl)oxolan-3-yl]oxyethyl acetate Structure

2-[(2R,3R,4R,5R...

4-O-(2,6-dimethylphenyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine Structure

4-O-(2,6-dimeth...

~%

2-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-(4-oxo-2-sulfanylidenepyrimidin-1-yl)oxolan-3-yl]oxyethyl acetate Structure

2-[(2R,3R,4R,5R...

2'-O-(2-oxoethyl)-4-O-(2,6-dimethylphenyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine Structure

2'-O-(2-oxoethy...

~%

2-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-(4-oxo-2-sulfanylidenepyrimidin-1-yl)oxolan-3-yl]oxyethyl acetate Structure

2-[(2R,3R,4R,5R...

2'-O-allyl-4-O-(2,6-dimethylphenyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine Structure

2'-O-allyl-4-O-...

~%

2-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-(4-oxo-2-sulfanylidenepyrimidin-1-yl)oxolan-3-yl]oxyethyl acetate Structure

2-[(2R,3R,4R,5R...

4-(2,6-dimethylphenoxy)-1-((6aR,8R,9R,9aR)-9-(2-hydroxyethoxy)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidin-2(1H)-one Structure

4-(2,6-dimethyl...

~%

2-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-(4-oxo-2-sulfanylidenepyrimidin-1-yl)oxolan-3-yl]oxyethyl acetate Structure

2-[(2R,3R,4R,5R...

2-(((6aR,8R,9R,9aR)-8-(4-(2,6-dimethylphenoxy)-2-thioxopyrimidin-1(2H)-yl)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl)oxy)ethyl acetate Structure

2-(((6aR,8R,9R,...

~%

2-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-(4-oxo-2-sulfanylidenepyrimidin-1-yl)oxolan-3-yl]oxyethyl acetate Structure

2-[(2R,3R,4R,5R...

2-(((6aR,8R,9R,9aR)-8-(4-(2,6-dimethylphenoxy)-2-oxopyrimidin-1(2H)-yl)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl)oxy)ethyl acetate Structure

2-(((6aR,8R,9R,...

~%

2-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-(4-oxo-2-sulfanylidenepyrimidin-1-yl)oxolan-3-yl]oxyethyl acetate Structure

2-[(2R,3R,4R,5R...

2'-O-(2,3-dihydroxypropyl)-4-O-(2,6-dimethylphenyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine Structure

2'-O-(2,3-dihyd...

~%

2-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-(4-oxo-2-sulfanylidenepyrimidin-1-yl)oxolan-3-yl]oxyethyl acetate Structure

2-[(2R,3R,4R,5R...

4-(2,6-dimethylphenoxy)-1-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)tetrahydrofuran-2-yl)pyrimidine-2(1H)-thione Structure

4-(2,6-dimethyl...

~79%

3’-O-(2-Methoxyethyl)-2-thiouridine Structure

3’-O-(2-Methoxy...

2'-O-(2-Methoxyethyl)uridine Structure

2'-O-(2-Methoxy...

~%

3’-O-(2-Methoxyethyl)-2-thiouridine Structure

3’-O-(2-Methoxy...

1-((2R,3R,4R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(2-methoxyethoxy)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

1-((2R,3R,4R,5R...

~%

3’-O-(2-Methoxyethyl)-2-thiouridine Structure

3’-O-(2-Methoxy...

N/A Structure

~%

3’-O-(2-Methoxyethyl)-2-thiouridine Structure

3’-O-(2-Methoxy...

1-((2R,3R,4R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(2-methoxyethoxy)tetrahydrofuran-2-yl)-4-(2,6-dimethylphenoxy)pyrimidine-2(1H)-thione Structure

1-((2R,3R,4R,5R...

~%

3’-O-(2-Methoxyethyl)-2-thiouridine Structure

3’-O-(2-Methoxy...