N2-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-3'-O-tert-butyldimethylsilyl guanosine Chemical Properties

Density 

1.25±0.1 g/cm3(Predicted)

storage temp. 

4°C, away from moisture and light

solubility 

DMSO : 100 mg/mL (129.88 mM; Need ultrasonic)

form 

Solid

pka

9.16±0.20(Predicted)

color 

White to off-white

InChIKey

XAIQBZNFPUNWMQ-HVXBIEPNNA-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](N2C3=C(C(NC(=N3)NC(=O)C(C)C)=O)N=C2)[C@H](O)[C@@H]1O[Si](C(C)(C)C)(C)C |&1:25,27,44,46,r|

N2-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-3'-O-tert-butyldimethylsilyl guanosine Usage And Synthesis

Uses

5'-DMT-3'-TBDMS-ibu-rG is is a modified nucleoside. 5'-DMT-3'-TBDMS-ibu-rG can be used in deoxyribonucleic acid synthesis.

Synthesis

Synthesis of 3'-DMTBS-5'-O-(4,4') tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide from tert-butyldimethylchlorosilane and N-(9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(1-hydroxy-2,2-bis(4-methoxyphenyl)-2-phenylethyl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide. -dimethoxytrityl)-N2-isobutyryl acylcytidine in the following general steps: to a solution of compound HLH (23.9 g, 36.450 mmol, 1.00 eq.) in N,N-dimethylformamide (120 mL) was added tert-butyldimethylchlorosilane (8.24 g, 54.675 mmol, 1.50 eq.) and 1H-imidazole ( 6.204 g, 91.124 mmol, 2.50 equiv). The reaction mixture was stirred at 25 °C overnight. After completion of the reaction, the reaction was quenched with methanol (5 mL) and the mixture was concentrated to give the residue. The residue was purified by preparative HPLC (mobile phase: water (containing 0.225% formic acid)-acetonitrile gradient elution) to afford compound LII (6.7 g, 24% yield) as a yellow solid.LC-MS analysis showed ESI-MS m/z 770.3 [M+H]+.

References

[1] Ezequiel Wexselblatt, et al. ppGpp analogues inhibit synthetase activity of Rel proteins from Gram-negative and Gram-positive bacteria. Bioorg Med Chem. 2010 Jun 15;18(12):4485-97. DOI:10.1016/j.bmc.2010.04.064

N2-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-3'-O-tert-butyldimethylsilyl guanosine(81256-89-5)Related Product Information

• 5'-O-DMTr-N2-isobutyrylguanosine
• N6-benzoyl-3'-O-t-butyldiMethylsilyl-5'-O-(4,4'-diMethoxytrityl)-adenosine
• 5'-O-DMT-2'-O-TBDMS-N-Bz-Adenosine
• 5'-DMT-RIBO ADENOSINE (N-BZ)
• 5'-O-DMT-2'-O-iBu-N-Bz-Guanosine