| Identification | Back Directory | [Name]
N2-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-3'-O-tert-butyldimethylsilyl guanosine | [CAS]
81256-89-5 | [Synonyms]
5'-DMT-3'-TBDMS-ibu-rG
5'-O-DMT-3'-O-TBDMS-ibu-rG
5'-O-DMT-3'-O-TBDMS-N2-IBU-RG
3'-O-tert-Butyldimethylsilyl-5'-O-DMT-N2-isobutyrylguanosine
N2-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-3'-O-tert-butyldimethylsilyl guanosine
Guanosine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-N-(2-methyl-1-oxopropyl)- | [Molecular Formula]
C41H51N5O8Si | [MDL Number]
MFCD00274105 | [MOL File]
81256-89-5.mol | [Molecular Weight]
769.96 |
| Chemical Properties | Back Directory | [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| |
| Hazard Information | Back Directory | [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 |
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