ChemicalBook CAS DataBase List 2'-Deoxyadenosine

2'-Deoxyadenosine synthesis

10synthesis methods

Product Name:2'-Deoxyadenosine
CAS Number:958-09-8
Molecular formula:C10H13N5O3
Molecular Weight:251.24

2'-deoxyadenosine synthesis: esterification of adenosine, acylation of an acylating agent and an acid binding agent to obtain an acylate; the obtained acylate is then subjected to reduction and purification to obtain 2'-deoxyadenosine. The esterification agent used in the esterification process is dialkyl tin oxide, 2'-O-p-toluenesulfonyladenosine is synthesized from adenosine, and 2'-deoxyadenosine is synthesized from 2'-O-p-toluenesulfonyladenosine glycosides.

9H-Purin-6-amine, 9-[2-deoxy-3,5-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-β-L-erythro-pentofuranosyl]-

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958-09-8
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Yield:958-09-8 91.2%

Reaction Conditions:

with tetrabutyl ammonium fluoride in tetrahydrofuran at 20; for 5 h;

Steps:

4 Example 4; 2'-Deoxyadenosine; Procedure D

To a solution of 2'-deoxy-3',5'-O-TIPDS-adenosine, (8A) (2.557 g, 5.18 mmol) in THF (15 mL) is added TBAF (10.4 mL, 1M in THF). The solution is stirred at room temperature for 5 hours. The solution is concentrated in vacuo and the residue is partitioned between water (100 mL) and dichloromethane (100 mL). The layers are separated and the aqueous layer is washed with dichloromethane (2×50 mL). The aqueous phase is concentrated in vacuo, and the residue is purified on a column of Dowex 1-X2 (OH^-) resin. The product is eluted with water, collected, evaporated and crystallized in ethanol to give 2'-deoxyadenosine (10A) (1.187 g, 91.2%). Melting point 190-19°2 C. ¹H NMR (DMSO) d 2.27 (ddd, J=13.2, 6.1, 2.8 Hz, 1, H_2'), 2.75 (ddd, J=13.2, 7.8, 5.8 Hz, 1, H₂), 3.60 (m,2, H_5',5), 3.90 (dd, J=6.6, 4.0 Hz, 1, H_3'), 4.43 (m, 1, H_4'), 5.27 (t, J=5.9 Hz, 1, OH_5'), 5.34 (d, J=3.9 Hz, 1, OH_3'), 6.37 (dd, J=6.1, 7.8 Hz, 1, H_1'), 7.35 (br s, 2, NH₂), 8.15 & 8.36 (s, s, 2, H_2,8). MS (FAB) m/z 252.1090 (MH⁺[C₁₀H₁₄N₅O₃]=252.1097.