5'-O-DMT-2'-TBDMS-Uridine Chemical Properties

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO : 100 mg/mL (151.32 mM; Need ultrasonic)

pka

9.39±0.10(Predicted)

form 

Solid

color 

White to light yellow

InChIKey

KVHQIELPHWJPSY-WLVJKCSANA-N

SMILES

O(C(C1=CC=C(OC)C=C1)(C1=CC=C(OC)C=C1)C1=CC=CC=C1)C[C@H]1O[C@@H](N2C=CC(=O)NC2=O)[C@H](O[Si](C(C)(C)C)(C)C)[C@@H]1O |&1:25,27,36,45,r|

5'-O-DMT-2'-TBDMS-Uridine Usage And Synthesis

Uses

5''-O-DMT-2''-TBDMS-Uridine (cas# 81246-80-2) is a nucleoside and has been used in the prepartion of pseudorotaxane architectures. It has also been able to undergo microwave-assisted phosphitylation in the preparation of nucleoside phosphoramidites.

Synthesis

5'-O-(4,4'-Dimethoxytrityl)uridine (27.88 g, 51.0 mmol) was dissolved in anhydrous tetrahydrofuran (340 mL). Anhydrous pyridine (16.2 mL, 0.20 mol) and silver nitrate (9.53 g, 56.1 mmol) were added sequentially under stirring and stirring was continued for 15 min. After silver nitrate was almost completely dissolved, tert-butyldimethylchlorosilane (TBDMS-Cl) (8.46 g, 56.1 mmol) was added quickly. The resulting turbid emulsion was stirred at room temperature for 12 hours. Upon completion of the reaction, the mixture was filtered into 5% sodium bicarbonate solution to prevent the shedding of 4,4'-dimethoxytrityl (DMTr) protecting group. Subsequently, the mixture was concentrated to about 200 mL on a rotary evaporator to remove some of the solvent. After dilution with ethyl acetate, the mixture was sequentially extracted three times with saturated sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated to dryness. Finally, the target product 5'-O-DMTr-2'-O-TBDMS-uridine (21.92 g, 65% yield) was purified by column chromatography (eluent: tert-butyl methyl ether/hexane, 0.50%). The product was structurally confirmed by 1H NMR (400 MHz, DMSO-d6) and mass spectrometry (calculated value: 546.20; measured value: 569.32 [M+Na]+).

References

[1] Organic Letters, 2013, vol. 15, # 18, p. 4710 - 4713
[2] Nature Chemistry, 2013, vol. 5, # 9, p. 790 - 795
[3] Tetrahedron Letters, 2011, vol. 52, # 20, p. 2575 - 2578

5'-O-DMT-2'-TBDMS-Uridine(81246-80-2)Related Product Information

• N-Acetyl-5′-O-[bis(4-methoxyphenyl)phenylmethyl]cytidine
• 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-FLUORO-D-URIDINE
• 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-O-METHYLURIDINE
• 2'-O-TBDMS-5'-O-DMT-N4-Ac cytidin
• 5'-O-(4,4'-Dimethoxytrityl)uridine