ChemicalBook CAS DataBase List Stavudine

Stavudine synthesis

9synthesis methods

Product Name:Stavudine
CAS Number:3056-17-5
Molecular formula:C10H12N2O4
Molecular Weight:224.21

4336-39-4
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3056-17-5
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Yield:3056-17-5 68%

Reaction Conditions:

Stage #1:(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate with palladium diacetate;lithium bromide in N,N-dimethyl-formamide at 180; for 36 h;Inert atmosphere;
Stage #2: with sodium methylate in methanol at 20; for 3 h;Concentration;Temperature;Reagent/catalyst;Solvent;

Steps:

8 Example 8Preparation of 2 ', 3'-didehydro-3'-deoxythymidine:
In a nitrogen atmosphere, to a 100 ml two-necked flask, 10 mmol was addedTriacetyl-5-methyluridine, 0.8 mmol of palladium acetate, 8 mmol of lithium bromide and 50 ml of N, N-dimethylformamide were charged and then a condenser was placed on a condenser and heated in an oil bath to 180 ° C. under magnetic stirring for 36 hours. Remove the oil bath, evaporate the reaction mixture, then add3 mmol sodium methoxide, and 50 mmol methanol, and stirred for 3 hours at room temperature. After the reaction was completed, the methanol was filtered and evaporated to dryness; the remaining solid was recrystallized from acetone, filtered and dried to give the product 2 ', 3'-didehydro-3'-deoxythymidine in 68% yield.

References:

Luoyang Normal College;Xu Chen;Li Hongmei;Wang Zhiqiang;Wang Chuanmin;Zheng Xiaobin CN106632554, 2017, A Location in patent:Paragraph 0011; 0012; 0013; 0014; 0015; 0016; 0017; 0018

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