223777-15-9

Usage

Uses

Used in Pharmaceutical Industry:
2'-O-(2-Methoxyethyl)uridine is used as a building block for cross-linking oligonucleotides for the development of novel therapeutic agents and drug delivery systems.
Used in Biotechnology Industry:
2'--O-(2-Methoxyethyl)uridine is used as a building block for cross-linking oligonucleotides to create advanced biotechnological products, such as modified nucleic acids and other bioactive molecules.

InChI:InChI=1/C12H18N2O7/c1-19-4-5-20-10-9(17)7(6-15)21-11(10)14-3-2-8(16)13-12(14)18/h2-3,7,9-11,15,17H,4-6H2,1H3,(H,13,16,18)/t7-,9+,10+,11-/m1/s1

Synthetic route

2-methoxy-ethanol (109-86-4) + 2,2'-Anhydrouridine (3736-77-4) → 2'-O-(2-methoxyethyl)uridine (223777-15-9)

Conditions	Yield
With aluminium for 48h; Etherification; Heating;	91%
Stage #1: 2-methoxy-ethanol With aluminium for 1h; Heating / reflux; Stage #2: 2,2'-Anhydrouridine for 48h; Heating / reflux; Stage #3: In ethanol; water for 0.166667h; Heating / reflux;	91%
With aluminium at 130℃; for 16h;	56%

uridine (58-96-8) → 2'-O-(2-methoxyethyl)uridine (223777-15-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 11.31 g / diphenyl carbonate; sodium hydrogen carbonate / N,N-dimethyl-acetamide / 5 h / 100 °C 2: 91 percent / aluminium / 48 h / Heating View Scheme

2-methoxy-ethanol (109-86-4) + 2,2'-Anhydrouridine (3736-77-4) → 2'-O-(2-methoxyethyl)uridine (223777-15-9)

Conditions	Yield
With aluminium for 48h; Etherification; Heating;	91%
Stage #1: 2-methoxy-ethanol With aluminium for 1h; Heating / reflux; Stage #2: 2,2'-Anhydrouridine for 48h; Heating / reflux; Stage #3: In ethanol; water for 0.166667h; Heating / reflux;	91%
With aluminium at 130℃; for 16h;	56%

uridine (58-96-8) → 2'-O-(2-methoxyethyl)uridine (223777-15-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 11.31 g / diphenyl carbonate; sodium hydrogen carbonate / N,N-dimethyl-acetamide / 5 h / 100 °C 2: 91 percent / aluminium / 48 h / Heating View Scheme

tert-butyldimethylsilyl chloride (18162-48-6) + 2'-O-(2-methoxyethyl)uridine (223777-15-9) → 1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-(2-methoxy-ethoxy)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (647839-16-5)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 12h;	86%

1-Methylpyrrolidine (120-94-5) + 4-nitro-phenol (100-02-7) + 2'-O-(2-methoxyethyl)uridine (223777-15-9) → 2'-O-(2-methoxyethyl)cytidine (223777-16-0)

Conditions	Yield
With chloro-trimethyl-silane; ammonia; trifluoroacetic anhydride In 1,4-dioxane; ethanol; acetonitrile	84%

2'-O-(2-methoxyethyl)uridine (223777-15-9) → 2'-O-(2-methoxyethyl)cytidine (223777-16-0)

Conditions	Yield
Stage #1: 2'-O-(2-methoxyethyl)uridine With 1-Methylpyrrolidine; chloro-trimethyl-silane In acetonitrile at 20℃; for 1h; Stage #2: With trifluoroacetic anhydride In acetonitrile at 0℃; for 0.0833333h; Stage #3: With 4-nitro-phenol; sodium bicarbonate; ammonia; water more than 3 stages;	84%
Multi-step reaction with 4 steps 1: 1-methylpyrrolidine / acetonitrile / 1 h / 20 °C 2: acetonitrile / 0.58 h / 0 °C 3: acetonitrile / 3 h / 0 °C 4: 5.07 g / conc. aq. NH3 / dioxane / 24 h / 55 °C View Scheme
Stage #1: 2'-O-(2-methoxyethyl)uridine With N-Methylpyrrole; chloro-trimethyl-silane In acetonitrile at 20℃; for 1h; Cooling with ice; Stage #2: With 4-nitro-phenol; trifluoroacetic anhydride at 0℃; for 3.5h;

2'-O-(2-methoxyethyl)uridine (223777-15-9) → 2'-O-(2-methoxyethyl)-5-iodouridine (1251827-55-0)

Conditions	Yield
With N-iodo-succinimide; 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 40℃; for 5h; Inert atmosphere;	78%

chloro-trimethyl-silane (75-77-4) + 2'-O-(2-methoxyethyl)uridine (223777-15-9) → 1-[(2R,3R,4R,5R)-3-(2-Methoxy-ethoxy)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl]-4-trimethylsilanyloxy-1H-pyrimidin-2-one

Conditions	Yield
With 1-Methylpyrrolidine In acetonitrile at 20℃; for 1h; silylation;

Upstream product

• 109-86-4 2-methoxy-ethanol 
• 3736-77-4 2,2'-Anhydrouridine 
• 58-96-8 uridine 

Downstream Products

• 223777-16-0 2'-O-(2-methoxyethyl)cytidine 
• 251647-51-5 5'-O-(4,4-dimethoxytrityl)-2'-MOE-uridine 
• 647839-22-3 1-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(2-methoxy-ethoxy)-tetrahydro-furan-2-yl]-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 647839-19-8 4-(2,6-Dimethyl-phenoxy)-1-[(2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-3-(2-methoxy-ethoxy)-tetrahydro-furan-2-yl]-1H-pyrimidine-2-thione 
• 647839-18-7 1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-(2-methoxy-ethoxy)-tetrahydro-furan-2-yl]-4-(2,6-dimethyl-phenoxy)-1H-pyrimidine-2-thione 
• 647839-17-6 1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-(2-methoxy-ethoxy)-tetrahydro-furan-2-yl]-4-(2,6-dimethyl-phenoxy)-1H-pyrimidin-2-one 

Relevant academic research and scientific papers

Conversion of uridine into 2'-O-(2-methoxyethyl)uridine and 2'-O-(2- methoxyethyl)cytidine

Reaction between aluminium 2-methoxyethoxide and 2,2'-anhydro-1-β-D- arabinofuranosyluracil 6 gives 2'-O-(2-methoxyethyl)uridine 9 in high yield. Compound 9 is converted into 2'-O-(2-methoxyethyl)cytidine 11 in good yield.

NUCLEIC ACID-POLYPEPTIDE COMPOSITIONS AND USES THEREOF

Disclosed herein are compositions and pharmaceutical formulations that comprise a binding moiety conjugated to a modified polynucleic acid molecule and a polymer. Also described herein include methods for treating a cancer which utilize a composition or a pharmaceutical formulation comprising a binding moiety conjugated to a polynucleic acid molecule and a polymer.

2′-Substituted RNA preparation

A process for the preparation of a compound of formula (1): is provided, which comprises the reaction a compound of formula (2): with a compound of formula Al(OR)3 under substantially anhydrous conditions. X, and X1 are each independently H or a protecting group, B is a base; R is an alkyl, alkoxyalkyl, alkenyl or alkynyl group, each of which may be optionally substituted, and L is a leaving group.

2'-SUBSTITUTED RNA PREPARATION

A process for the preparation of a compound of formula (1): is provided, which comprises the reaction a compound of formula (2): with a compound of formula Al(OR)3 under substantially anhydrous conditions. X, and X1 are each independently H or a protecting group, B is a base; R is an alkyl, alkoxyalkyl, alkenyl or alkynyl group, each of which may be optionally substituted, and L is a leaving group.