Deoxyadenylyl-(3'-5')-phosphoro-o-chlorophenyl deoxyadenosine having the Sp configuration was synthesised stereoselectively by condensing N,5'-bis-dimethoxytrityldeoxyadenosine 3'-(o-chlorophenyl) phosphate with N,3'-bis-dimethoxytrityldeoxyadenosine using 1-2,4,6-triisopropylbenzene-5-(pyridin-2-yl) tetrazole as the activating reagent followed by dedimethoxytritylation. The absolute configuration of
通过将N,5′-双-二甲氧基三苯甲基脱氧
腺苷3′-(邻
氯苯基)
磷酸酯与N,3′-双-缩合缩合,立体选择性地合成具有Sp构型的脱氧
腺苷基-(3′-5′)-
磷酸-邻
氯苯基脱氧
腺苷。使用1-2,4,6-
三异丙基苯-5-(
吡啶-2-基)
四唑作为活化剂的二甲氧基三苯甲基脱氧
腺苷,然后进行二甲氧基三苯甲基化。该非对映异构体的绝对构型是通过光谱比较两个相应的非对映异构体而确定的,这两个非对映异构体是使用常规的缩合试剂制备的,并通过
硅胶色谱法进行分离。仅当通过立体选择性合成获得的产物具有Sp构型时,才能解释它们在质子磁共振中的核Overhauser效应和这两种非对映异构体的圆二色性。