Synthesis of N,O-protected derivatives of 2′-O-methylcytidine and of 2′-O-methyl- and N1-methylguanosines

Gladkaya, A. V.; Levitskaya, Z. V.; Shalamai, A. S.; Usenko, L. S.; Dashevskaya, T. A.

doi:10.1007/bf00597663

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2024

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“…The solution was concentrated under reduced pressure and purified by reversed phase column chromatography (C18, elute: MeOH/H 2 O = 5/95–15/85) to give 1-methylguanosine m 1 G as a white solid (24.9 mg, yield 84%). 1 H NMR (300 MHz, DMSO- d 6 ): δ 7.94 (s, 1H), 7.03 (s, 2H), 5.71 (d, J = 6.0 Hz, 1H), 5.38 (d, J = 5.9 Hz, 1H), 5.12 (d, J = 4.5 Hz, 1H), 5.02 (t, J = 5.4 Hz, 1H), 4.40 (d, J = 5.0 Hz, 1H), 4.11 (d, J = 5.1 Hz, 1H), 3.87 (d, J = 4.0 Hz, 1H), 3.66–3.51 (m, 2H), 3.32 (s, 3H) …”

Section: Methodsmentioning

confidence: 99%

Selective Methylation of Nucleosides via an In Situ Generated Methyl Oxonium

Jin,

He,

Hui

et al. 2024

J. Org. Chem.

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A very mild and efficient procedure has been developed for the preparation of N-methylated uridine, pseudouridine, guanosine and inosine derivatives. This process was compatible with free hydroxyls within the ribose and did not require precautions on the protection or deprotection of other functionalities. The key to this extremely mild methylation without protection relied on the in situ generated methyl oxonium from the Wittig reagent and methanol. A putative mechanism for the selective methylation was also proposed.

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Section: Methodsmentioning

confidence: 99%