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首页> 外文期刊>RSC Advances >Synthesis of protected 2 '-O-deoxyribonucleotides on a precipitative soluble support: a useful procedure for the preparation of trimer phosphoramidites
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Synthesis of protected 2 '-O-deoxyribonucleotides on a precipitative soluble support: a useful procedure for the preparation of trimer phosphoramidites

机译：在沉淀的可溶性载体上合成受保护的2'-O-脱氧核糖核苷酸：制备三聚亚磷酰胺的有用方法

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摘要

Tetrakis-O-(4-azidomethylphenyl)pentaerythritol, derivatized with 5'-O-(4,4'-dimethoxytrityl)-3'-O-{4-[2-(but-3-yn-1-ylamino)-2-oxoethoxy]phenoxyacetyl}thymidine, was used as a soluble support to assemble fully protected 2'-O-deoxyribonucleotide trimers by the phosphotriester chemistry. After the coupling and detritylation steps, the support-bound construct was purified by precipitation in MeOH. The trimers (TAT, AGT, TTA, CAT, GCT), in fully protected form, were released by a treatment with dilute methanolic K2CO3 and filtered through a short silica gel column in 65-70% overall yield. Two of the trimers (CAT and GCT), prepared in 0.5 mmol scale, were converted to the corresponding phosphoramidites. The entire procedure for the preparation of trimer phosphoramidites proved straightforward and applicable for the large scale synthesis.
机译：用5'-O-（4,4'-二甲氧基三苯甲基）-3'-O- {4- [2-（2-（but-3-yn-1-ylamino）-）衍生的四-O-（4-叠氮甲基苯基）季戊四醇2-氧乙氧基]苯氧基乙酰基}胸苷被用作可溶性载体，以通过磷酸三酯化学组装完全保护的2'-O-脱氧核糖核苷酸三聚体。在偶联和去三苯甲基化步骤之后，通过在MeOH中沉淀来纯化与载体结合的构建体。完全保护形式的三聚体（TAT，AGT，TTA，CAT，GCT）通过用稀甲醇K2CO3处理而释放，并通过短硅胶柱过滤，总产率为65-70％。将以0.5 mmol规模制备的两个三聚体（CAT和GCT）转化为相应的亚磷酰胺。事实证明，制备三聚亚磷酰胺的整个过程是直接的，可用于大规模合成。

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