ChemicalBook CAS DataBase List 2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl-

2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl- synthesis

7synthesis methods

Product Name:2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl-
CAS Number:97614-47-6
Molecular formula:C24H21FN2O7
Molecular Weight:468.4312

2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate

97614-44-3
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7288-28-0
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2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl-

97614-47-6
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Yield:97614-47-6 70 g

Reaction Conditions:

in tetrachloromethane at 80; for 48 h;

Steps:

a.18 Preparation of compound 28-3:

To a solution of 28-2 (73 g, 0.173 mol) in CCl₄(500 mL) was added 28a (70 g, 0.259 mol) at room temperature and the mixture was heated to 80^oC and stirred at this temperature for 48 hours. The 28-2 was consumed and major desired product were detected by TLC and LC-MS. The reaction was poured to water (1000 mL) and extracted with DCM (300 mL *3). The combined organic layers were washed with (500 mL * 2), brine (1000 mL), dried over anhydrous Na₂SO₄and evaporated in thevacuo to give crude product, which was purified by column chromatography with a gradient of 10 to 35% EtOAc in PE to give 28-3 (70 g, 149.44 mmol, 86.6% yield) as white solid.¹H NMR (400 MHz, CDCl₃) δ 9.49 (s, 1H), 8.10 (dd, J = 16.7, 7.9 Hz, 4H), 7.72 - 7.57 (m, 2H), 7.49 (dt, J = 11.6, 7.7 Hz, 4H), 7.38 (s, 1H), 6.39 (dd, J = 22.1, 2.6 Hz, 1H), 5.66 (dd, J = 17.9, 2.6 Hz, 1H), 5.36 (dd, J = 50.2, 2.6 Hz, 1H), 4.83 (qd, J = 12.2, 4.0 Hz, 2H), 4.51 (d, J = 3.4 Hz, 1H), 1.77 (s, 3H). ESI-MS: m/z 469.0 [M+H]⁺.

References:

WO2021/119325,2021,A1 Location in patent:Paragraph 0056; 0333

97614-43-2 Synthesis