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腺苷类似物1-脱氮腺苷(1)具有广泛的生物活性,有抑制血小板凝聚和腺苷脱氨酶的作用。本文介绍1的新合成方法。合成路线如方程式所示。化合物2与硝酸-三氟醋酸混合物反应生成7-硝基咪唑并[4.5-6]吡啶4-氧化物(3)。和PCl_3处理3,生成脱氧衍生物4。在催化量的SnCl_4作用下,4再与等摩尔的1,2,3,5-四-O-乙酰基-β- D映喃核糖(TAR)进行反应,得到7-硝基-3-(2,3,5-三-O-乙酰基-β-D-呋喃核糖)-3H咪唑并[4,5-b]吡啶(5),收率82%。在化合物5的甲醇溶液中通入氨气,脱去保护基,生成化合物6,收率86%。用Pd/C加压氢化,
Adenosine analog 1-deazaadenosine (1) has a wide range of biological activity, inhibition of platelet aggregation and adenosine deaminase role. This article describes a new synthesis method. The synthetic route is shown in the equation. Compound 2 is reacted with a nitric acid-trifluoroacetic acid mixture to produce 7-nitroimidazo [4.5-6] pyridine 4-oxide (3). And PCl_3 treatment 3, deoxy derivative 4 was generated. Reaction of 4 with an equimolar amount of 1,2,3,5-tetra-O-acetyl-β-D-D-ribose ribose (TAR) under the action of a catalytic amount of SnCl_4 gave 7-nitro-3- Tri-O-acetyl-β-D-ribofuranosyl) -3H imidazo [4,5-b] pyridine (5) was obtained in 82% yield. Ammonia gas was bubbled through the methanol solution of compound 5 to remove the protecting group to produce compound 6 in a yield of 86%. Hydrogenation with Pd / C,