ChemicalBook CAS DataBase List 2'-C-Methyluridine

2'-C-Methyluridine synthesis

12synthesis methods

Product Name:2'-C-Methyluridine
CAS Number:31448-54-1
Molecular formula:C10H14N2O6
Molecular Weight:258.23

23643-36-9 Synthesis

2'-C-Methyl-, 2',3',5'-tribenzoateuridine

23643-36-9
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31448-54-1
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Yield:31448-54-1 99.6%

Reaction Conditions:

with ammonia in methanol at 45; for 18 h;Sealed tube;High pressure;

Steps:

1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-2-yl]pyrimidine-2,4-dione (2, 2’-C-β-methyluridine, 2’-MeU)

A 500-mL heavy wall pressure vessel was charged with a stir bar,[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-4-methyl-tetrahydrofuran-2-yl]methylbenzoate (43.70 g, 76.59 mmol), methanol (50 mL), and lastly ammonia (300 mL, 2100 mmol) as a 7Nsolution in methanol (300 mL). The vessel was sealed, and the thick white suspension was heated to 45oC for 18 hours, over which time the solid dissolved. The next day, the reaction was concentrated todryness. The resulting mixture was triturated with MTBE, filtered, and further washed with MTBE. Theresulting white amorphous solid was collected and dried in a vacuum oven at 45°C overnight to afford thedesired product (19.7 g, 99.6% yield); 1H NMR in D2O conformed to that previously reported.

References:

Dentmon, Zackery;Butch, Christopher;Gold, Hannah Beth;Liotta, Dennis [Synlett,2022]