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

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 Information

Hazard Codes 

Xn

Risk Statements 

20/22-36/37/38

Safety Statements 

22-26-36

WGK Germany 

3

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich

5'-O-(4,4'-Dimethoxytrityl)-2'-deoxyuridine Usage And Synthesis

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

5'-O-(4,4'-Dimethoxytrityl)-2'-deoxyuridine(23669-79-6)Related Product Information

• Doxifluridine
• 2'-Deoxyuridine
• 4-Methoxyphenylacetone
• (Trifluoromethoxy)benzene
• Benzyl alcohol
• Benzyl benzoate
• Trifluridine
• Benzyl bromide
• Uridine
• DMT-2′O-TBDMS-rU Phosphoramidite
• BrdU (Bromodeoxyuridine)
• uridine diphosphate glucose {= UDP-glucose}
• DNA, SINGLE STRANDED, IMM. ON CELLULOSE, FROM CALF THYMUS*
• DMT-2'O-Methyl-rU Phosphoramidite
• 5'-O-(4,4'-Dimethoxytrityl)uridine
• DMT-dT Phosphoramidite
• 5'-O-Dimethoxytrityl-deoxythymidine
• 5'-O-(4,4'-Dimethoxytrityl)-thymidine-3'-O-succinic acid