ChemicalBook CAS DataBase List 1-[5-O-[Bis(4-methoxyphenyl)phenylmethyl]-2-deoxy-2-fluoro-beta-D-arabinofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione

1-[5-O-[Bis(4-methoxyphenyl)phenylmethyl]-2-deoxy-2-fluoro-beta-D-arabinofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione synthesis

6synthesis methods

Product Name:1-[5-O-[Bis(4-methoxyphenyl)phenylmethyl]-2-deoxy-2-fluoro-beta-D-arabinofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione
CAS Number:144822-48-0
Molecular formula:C31H31FN2O7
Molecular Weight:562.59

40615-36-9 Synthesis

40615-36-9
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69256-17-3 Synthesis

1-[(2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

69256-17-3
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1-[5-O-[Bis(4-methoxyphenyl)phenylmethyl]-2-deoxy-2-fluoro-beta-D-arabinofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione

144822-48-0
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Yield:144822-48-0 92%

Reaction Conditions:

with pyridine at 20; for 2 h;

Steps:

a.18 Preparation of compound 28-5:

To a solution of 28-4 (35 g, 134.50 mmol) in dry pyridine (300 mL) was added DMTrCl (54.7 g, 161.4 mmol) at room temperature and the mixture was stirred at this temperature for 2 hours until 28-4 was consumed and major 28-5 was detected by TLC and LC-MS. The reaction was quenched with CH₃OH/H₂O (20 mL/500 mL) and the mixture was extracted with EA (300 mL *3), combined organic layers were washed water (500 mL * 2), brine (1000 mL), dried over anhydrous Na₂SO₄and evaporated in the vacuo to give crude product, which was purified by column chromatography with a gradient of 10 to 60% EtOAc in PE to give 28-5 (69.7 g, 123.78 mmol, 92.0% yield) as white solid. ESI-MS: m/z 585.1 [M+Na]⁺.

References:

WO2021/119325,2021,A1 Location in patent:Paragraph 0056; 0335