5'-O-(4,4'-Dimethoxytrityl)-2'-deoxyuridine

5'-O-(4,4'-Dimethoxytrityl)-2'-deoxyuridine Property

Melting point:

120 °C

Density 

1.294±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Soluble in acetonitrile at 20mg/ml

form 

Powder

pka

9.39±0.10(Predicted)

color 

White to Off-white

optical activity

7.03°(C=0.01g/mI, DMF, 20°C, 589nm)

Safety

Hazard Codes 

Xn

Risk Statements 

20/22-36/37/38

Safety Statements 

22-26-36

WGK Germany 

3

HS Code 

29349990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H301Toxic if swalloed

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

5'-O-(4,4'-Dimethoxytrityl)-2'-deoxyuridine Chemical Properties,Usage,Production

Chemical Properties

solid

Uses

It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Synthesis

To a solution of 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (22.80 g, 99.91 mmol) in anhydrous pyridine (200 mL) was added 4,4'-bis(methoxytrityl)chlorine (37.24 g, 109.90 mmol) and the mixture was allowed to stand at 25 °C for 12 hours. Upon completion of the reaction, the reaction was quenched with saturated NaHCO3/NH4Cl solution (200 mL) and subsequently extracted with ethyl acetate (3 x 200 mL). The organic layers were combined, washed with brine (2 x 100 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (petroleum ether: ethyl acetate, 2:1 to 0:1) to afford the target product 1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (43.00 g, 72.94 mmol) as yellow foam.

References

[1] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 10, p. 1649 - 1658
[2] Organic letters, 2003, vol. 5, # 6, p. 917 - 919
[3] Journal of the American Chemical Society, 2001, vol. 123, # 15, p. 3405 - 3411
[4] Chemical Research in Toxicology, 2006, vol. 19, # 7, p. 968 - 976
[5] Nucleic Acids Research, 2015, vol. 43, # 11, p. 5275 - 5283