Synthesis method of 2-deoxy-beta-adenosine
A synthesis method and adenosine technology are applied in the synthesis field of 2-deoxy-β-adenosine, can solve the problems of unavoidable chromatographic separation method, low yield, and cannot be suitable for industrial production, and achieve cost reduction, process simplification, Yield and stereoselectivity enhancement effect
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example 1
[0016] Example 1: Synthesis of 1-chloro-2-deoxy-3,5-O-di(p-chlorobenzoyl)-ribose
[0017] Dissolve 0.96 g of deoxyribose in 18 ml of anhydrous methanol, add 0.07 ml of 1mol / L dry hydrogen chloride methanol solution, keep warm at 25°C and stir for 1 hour or add 0.20 ml of 1mol / L dry hydrogen chloride methanol solution, keep warm at 25°C and stir for 0.5 hour , add 0.015 g of sodium bicarbonate, stir for 1 hour, spin dry, add 2 ml of toluene and 2 ml of pyridine, spin dry, the resulting syrup is dissolved in 5 ml of pyridine, cooled to 0 ° C, quickly dropwise add 2.1 ml of Chlorobenzoyl chloride, keep warm at 40°C for 3 hours, add 20 ml of water and 20 ml of isopropyl ether, stir for a while, transfer to a separatory funnel, shake well, let stand, separate the ether layer, and use about 60 ml of 5% Wash with dilute sulfuric acid 4 times, then wash once with about 50 ml of 5% sodium bicarbonate solution, and dry over anhydrous magnesium sulfate.
[0018] Filtrate, pass through a...
example 2
[0019] Example 2: Preparation of adenine sodium salt
[0020] Add 0.493g of adenine and 0.139g of sodium hydroxide to 15ml of anhydrous methanol, heat, and after the solid is completely dissolved, reflux for 1 hour, spin dry, add a small amount of anhydrous toluene for azeotropic dehydration twice, and obtain 0.573g of adenine sodium salt, It is a white powder with a yield of 100%.
example 3
[0021] Example 3: Undeprotected 2-deoxy β-adenosine
[0022] Suspend 0.43g of adenine sodium salt in 15ml of methyl ethyl ketone, add 0.784g of 1-chloro-2-deoxy-3,5-O-di(p-chlorobenzoyl)-ribose, stir at room temperature for 4 hours, then add some The ethyl acetate was stirred for 10 hours. Then the suspension was washed with water and saturated brine, the solvent was evaporated to dryness, added toluene, heated to dissolve, cooled to room temperature with stirring, filtered with suction, and the filtrate was evaporated to dryness to obtain 0.530 g of a white waxy solid with a yield of 55%.
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