N6-Benzoyl-2'-O-Methoxyethyladdenosine synthesis
- Product Name:N6-Benzoyl-2'-O-Methoxyethyladdenosine
- CAS Number:333335-93-6
- Molecular formula:C20H23N5O6
- Molecular Weight:429.43
Yield:333335-93-6 87.1%
Reaction Conditions:
Stage #1: 2'-O-(2-methoxyethyl)adenosinewith pyridine;chloro-trimethyl-silane for 1.33333 h;Inert atmosphere;Cooling with ice;
Stage #2: benzoyl chloride for 2 h;
Steps:
1 Synthesis of 2’-O-Methoxyethyl-N6-Benzoyl-adenosine
The compound 2'-O-MOE-adenosine (2.0 g, 1 eq) was taken, Using anhydrous pyridine 7mL With water twice, Add 10mL anhydrous pyridine to dissolve, The mixture was stirred in an ice bath for 20 min under nitrogen. Trimethylchlorosilane (4.7 mL, 8 eq) was added, After stirring for 60 min, benzoyl chloride (1.1 mL, 1.5 eq) was added, Stirring was continued for 120 min, After removing the ice bath and stirring for 30 min at room temperature, Add ice water 3mL, Stirring 30min then concentrated ammonia 5mL room temperature stirring 30min. The reaction mixture was concentrated and partitioned between methylene chloride and saturated brine, The dichloromethane phase was dried over anhydrous sodium sulfate overnight, Concentrated, and separated by column chromatography to give 2.3 g of a product in a yield of 87.1%
References:
CN106117289,2016,A Location in patent:Paragraph 0042; 0043
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