ChemicalBook CAS DataBase List 2'-Deoxycytidine

2'-Deoxycytidine synthesis

11synthesis methods

Product Name:2'-Deoxycytidine
CAS Number:951-77-9
Molecular formula:C9H13N3O4
Molecular Weight:227.22

Acetamide, N-[1-(2-deoxy-β-L-erythro-pentofuranosyl)-1,2-dihydro-2-oxo-4-pyrimidinyl]-

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Yield:951-77-9 84.6%

Reaction Conditions:

in methanol;

Steps:

10 Example 10; 2'-Deoxycytidine

2'-deoxy-4-N-acetylcytidine is treated with methanolic ammonia overnight. The solution is concentrated in vacuo, and the residue is dissolved in water (100 mL) and is washed with dichloromethane (2×50 mL). The aqueous phase is evaporated in vacuo and the residue is purified on a column of Dowex 1-X2 (OH^-)resin. The product is eluted with water, and the fractions are collected, evaporated and the residue is crystallized in methanol to give 2'-deoxycytidine (0.902 g, 84.6%). Melting point 208-210° C. ¹H NMR (DMSO) d 1.94(dt, J=13.2, 6.1 Hz, 1, H_2'), 2.12 (ddd, J=13.2, 6.0, 3.3 Hz, 1, H₂),3.07 (m, 2, H_5',5), 3.77 (dd, J=6.9, 3.8 Hz, 1, H_3'), 4.21 (dd, J=5.9, 3.2 Hz, 1, H_4'), 5.02 (t, J=5.0 Hz, 1, OH_5'), 5.23 (d, J=4.1 Hz, 1, OH_3'), 5.75 (d, J=7.4 Hz, 1, H₅), 6.17 (t, J=6.7 Hz, 1, H_1'), 7.21 (br s, 2, NH₂), 7.81 (d, J=7.4 Hz, 1, H₆) ppm. MS (FAB) m/z 228.0990 (MH⁺[C₉H₁₄N₃O₄]=228.0984).