ChemicalBook CAS DataBase List 3'-deoxyinosine

3'-deoxyinosine synthesis

8synthesis methods

Product Name:3'-deoxyinosine
CAS Number:13146-72-0
Molecular formula:C10H12N4O4
Molecular Weight:252.23

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13146-72-0
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Yield:13146-72-0 288 mg

Reaction Conditions:

with ammonium hydroxide in methanol at 20; for 1 h;

Steps:

3′-Deoxyinosine (8)

25% Aq NH3 (12 mL) was added to a solution of diacetate 7 (0.6 g (1.80mmol) in MeOH (6 mL) and the mixture was stirred at r.t. After 1 h, the deacetylation was complete [TLC monitoring CHCl3/MeOH (9:1)], the mixture was evaporated to dryness and the target product was isolated by a column chromatography (Separon, 1.8 × 25 cm, gradient MeOH/H2O 0 → 30%, 0.8 L, flow rate 6 mL/min) as a lyophilized powder; yield: 288 mg (1.14 mmol, 63%); purity 98.6%; HPLC (method I); tR = 6.95 min. 1H NMR (700 MHz, DMSO-d6): δ = 12.32 (s, 1 H, NH), 8.32 (s, 1 H, H-8), 8.05 (s, 1 H, H-2), 5.86 (d, J = 1.2 Hz, 1 H, H-1′), 5.66 (d, J = 3.4 Hz, 1H, OH-2′), 5.00 (d, J = 5.1 Hz, 1 H, OH-5′), 4.51 (m, 1 H, H-2′), 4.36 (m,1 H, H-4′), 3.69 and 3.53 (2 m, 2 H, H-5′), 2.21 (ddd, J = 13.1, 9.3, 5.9Hz, 1 H, H-3a′), 1.90 (ddd, J = 13.1, 5.9, 2.3 Hz, 1 H, H-3b′). 13C NMR (176 MHz, DMSO-d6): δ = 157.20 (C=O), 148.12 (C4), 146.30(C2), 138.50 (C8), 124.70 (C5), 91.15 (C1′), 81.43 (C4′), 75.49 (C2′),62.70 (C5′), 34.29 (C3′). 15N NMR (71 MHz, DMSO-d6): δ = 249.30 (N7), 214.58 (N3), 178.25(N9), 174.55 (N1). HRMS (ESI+): [M + H]+ calcd for C10H13N4O4: 253.0937; found: 253.0949; m/z [base + H]+ calcd for C5H5N4O: 137.0463; found:137.0491; m/z [M + Na]+ calcd for C10H12N4NaO4: 275.0756; found: 275.0799; m/z [2 M + H]+ calcd for C20H25N8O8: 505.1795; found: 505.1815; m/z [3 M + H]+ calcd for C30H37N12O12: 757.2654; found:757.2656.UV (H2O, pH 7.0): λ (ε): 248 (12,100, max), 224 nm (4,500, min) [Lit.7bUV (H2O, pH 7.0): λ = 250.5 nm (11,300, max)].

References:

Denisova, Alexandra O.;Tokunova, Yulia A.;Fateev, Ilja V.;Breslav, Alexandra A.;Leonov, Vladimir N.;Dorofeeva, Elena V.;Lutonina, Olga I.;Muzyka, Inessa S.;Esipov, Roman S.;Kayushin, Alexey L.;Konstantinova, Irina D.;Miroshnikov, Anatoly I.;Stepchenko, Vladimir A.;Mikhailopulo, Igor A. [Synthesis,2017,vol. 49,# 21,p. 4853 - 4860]

58-63-9 Synthesis