2-chloro-3'-deoxyadenosine synthesis

13146-72-0 Synthesis

13146-72-0
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1839-18-5
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68-94-0 Synthesis

68-94-0
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115044-75-2
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Yield:115044-75-2 40%

Reaction Conditions:

with potassium dihydrogenphosphate;recombinant E_. coli purine nucleoside phosphorylase in water at 50; pH=7; for 192 h;Enzymatic reaction;

Steps:

2-Chloro-9-(3-deoxy-β-D-ribofuranosyl)adenine (9)

2-Chloroadenine (50 mg, 0.295 mmol) was dissolved in H2O (660 mL) under heating and stirring. The solution was cooled to 50 °C, 3′-deoxyinosine (8, 0.1 g, 0.396 mmol) and KH2PO4 (180 mg, 1.323 mmol) were added, and the pH of the mixture was adjusted to 7.0 (2.0 mM); PNP (1320 IU) was added and the mixture was incubated at 50 °C for 8 d under stirring. The precipitate was filtered off, the solution was concentrated and the desired product was isolated by column chromatography (silica gel 100 C18-RP, 2.5 × 19 cm, 10% aq EtOH, flow rate 5 mL/min) as a lyophilized powder; yield: 34 mg (0.119 mmol, 40%); purity 99.3%; HPLC (method II); tR = 11.41 min. 1H and 13C NMR spectra are in agreement with the literature data. 1H NMR (700 MHz, DMSO-d6): δ = 8.38 (s, 1 H, H-8), 7.77 (s, 2 H, NH2), 5.81 (d, J = 1.9 Hz, 1 H, H-1′), 5.66 (br s, 1 H, OH-2′), 4.99 (m, 1 H, OH- 5′), 4.53 (m, 1 H, H-2′), 4.36 (m, 1 H, H-4′), 3.69 and 3.53 (2 m, 2 H, H- 5′), 2.22 (ddd, J = 13.1, 8.9, 5.7 Hz, 1 H, H-3a′), 1.91 (ddd, J = 13.1, 6.1, 2.8 Hz, 1 H, H-3b′). 13C NMR (176 MHz, DMSO-d6): δ = 157.18 (C6), 150.36 (C4), 139.83 (C8), 118.55 (C5), 91.15 (C1′), 81.36 (C4′), 75.17 (C2′), 62.77 (C5′), 34.21 (C3′). 15N NMR (71 MHz, DMSO-d6): δ = 241.41 (N7), 220.38 (N3), 174.09 (N9), 86.94 (NH2). HRMS (ESI+): m/z [M + H]+ calcd for C10H13N5O3Cl: 288.0677/286.0707, 37Cl/35Cl; found: 288.0691/286.0721, 37Cl/35Cl; m/z [base + H]+ calcd for C5H5N5Cl: 172.0204/170.0233, 37Cl/35Cl; found: 172.0219/170.0249, 37Cl/35Cl. UV (H2O, pH 7.0): λ (ε) = 264 (12,100, max), 232 nm (4,700, min) [Lit.9 UV (H2O): λ = 265 nm (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]

Adenosine, 2-chloro-3'-deoxy-, 2'-acetate 5'-benzoate

1504571-49-6
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115044-75-2
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146-77-0 Synthesis

146-77-0
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115044-75-2
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Adenosine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2-chloro- (9CI)

119530-57-3
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115044-75-2
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65870-99-7
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68-94-0 Synthesis

68-94-0
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115044-75-2
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References