ChemicalBook CAS DataBase List 2'-O-Methyl-N2-methylguanosine

2'-O-Methyl-N2-methylguanosine synthesis

3synthesis methods

Product Name:2'-O-Methyl-N2-methylguanosine
CAS Number:135023-21-1
Molecular formula:C12H17N5O5
Molecular Weight:311.29

Guanosine, 2'-O-methyl-N-[[(4-methylphenyl)thio]methyl]-, 3',5'-diacetate

1613530-50-9
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135023-21-1
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Yield:135023-21-1 43%

Reaction Conditions:

Stage #1: C₂₃H₂₇N₅O₇Swith sodium tetrahydroborate in dimethyl sulfoxide at 100;
Stage #2: with acetic acid in ethanol at 20;

Steps:

55 Synthesis of N²,2'-0-dimethylguanosine (00901072014):

Sodium borohydride (0.7 g, 18.0 mmol) was added to a solution of compound 175 (3.0 g, 5.8 mmol) in dimethyl sulfoxide (15 m L). The reaction mixture was heated at 100 °C for 1 -2 hr, and then cooled to room temperature. It was then quenched with acetic acid/ethanol (50 m l_, v : v = 1 :1 0). The resulted colorless precipitate was filtrated out, and washed thoroughly with methanol. The crude product was dried under reduced pressure, and water was added. After further evaporation of water, the residue was crystallized from water to give N², 2'-dimethylguanosine 177 as a white solid (0.62 g, 43%). HPLC purity: 98 %, ESI mass spectrum m/z 312.8 [M + H]⁺ , 623 [2M + 1 ]⁺, ¹ H NMR (300MHz, DMSO-d6) δ 1 .85 (br, 1 H ), 7.93 (s, 1 H), 7.60( br, 1 H), 5.84 (d, J = 3.9Hz, 1 H ), 4.82- 5.10 (br, 2H), 4.26-4.29 (m , 2H), 3.90 (s, 1 H), 3.53-3.57 (m , 2H), 3.35(s, 3H), 2.78 (s, 3H). ESI mass spectrum m/z 312 (M + H)⁺, 623 (2M + H)⁺. UV, -max = 258 nm.

References:

WO2014/93924,2014,A1 Location in patent:Page/Page column 297; 298

2140-71-8 Synthesis

2140-71-8
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135023-21-1
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References

Guanosine, 2'-O-methyl-, 3',5'-diacetate

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135023-21-1
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References