2'-Deoxycytidine monohydrate synthesis
- Product Name:2'-Deoxycytidine monohydrate
- 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]-](/CAS/20210305/GIF/380887-00-3.gif)
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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, H2'), 2.12 (ddd, J=13.2, 6.0, 3.3 Hz, 1, H2),3.07 (m, 2, H5',5), 3.77 (dd, J=6.9, 3.8 Hz, 1, H3'), 4.21 (dd, J=5.9, 3.2 Hz, 1, H4'), 5.02 (t, J=5.0 Hz, 1, OH5'), 5.23 (d, J=4.1 Hz, 1, OH3'), 5.75 (d, J=7.4 Hz, 1, H5), 6.17 (t, J=6.7 Hz, 1, H1'), 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).
References:
US6822089,2004,B1 Location in patent:Page column 14
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