N⁶-benzoyl-5'-O-benzoyl-2'-deoxyadenosine | 104769-16-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N⁶-benzoyl-5'-O-benzoyl-2'-deoxyadenosine
• 英文别名: N⁶,5'-dibenzoyl-2'-deoxyadenosine；N6,5'-O-dibenzoyl-2'-deoxyadenosine；[(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-3-hydroxyoxolan-2-yl]methyl benzoate
• CAS: 104769-16-6
• 化学式: C₂₄H₂₁N₅O₅
• 分子量: 459.461
• InChiKey: INUFEIRTCLFJBN-IPMKNSEASA-N

物化性质

• 熔点：
  165-167 °C
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N⁶-benzoyl-5'-O-benzoyl-2'-deoxyadenosine 在 三氟乙酸 作用下， 生成 卡培他滨杂质25
  参考文献：
  名称：

  核碱基和糖部分的保护基对2个脱氧腺苷糖苷酸性的水解作用

  摘要：

  在不同浓度的氧鎓离子下，测量了几种6-取代的2个脱氧腺苷的水解速率常数，以评估各种6-和糖保护基在核酸合成中遇到的脱嘌呤反应中的作用。通过在不存在和存在三氟乙酸的情况下在DMSO- 6中记录15 N NMR光谱来确定质子化的位点。6-酰基-2脱氧腺苷的单阳离子的异常不稳定性是由优选的7个质子化引起的。

  DOI：

  10.1016/s0040-4020(01)90322-9
• 作为产物：
  描述：

  N2-异丁酰基-2′-脱氧鸟苷 在 双(2-氧代-3-恶唑烷基)次磷酰氯 作用下， 以 吡啶 为溶剂， 反应 8.0h， 生成 N⁶-benzoyl-5'-O-benzoyl-2'-deoxyadenosine
  参考文献：
  名称：

  通过op n，n-双-（2-氧代-恶唑烷-3-基）磷二酰胺氯化物（bopdc）对脱氧核糖核苷进行化学和区域选择性酰化

  摘要：

  在N，N-双-（2-氧代-恶唑烷-3-基）磷二酰胺基氯化物（BOPDC）活化后，通过用羧酸直接将底物酰化，可获得高产率的5'-酰基-脱氧核糖核苷。在相同的实验条件下，可以进行未保护的脱氧腺苷的化学选择性苯甲酰化。已经从由此获得的碱基不稳定的5'-保护的核苷制备了核苷酸构件。

  DOI：

  10.1016/s0040-4020(01)85111-5

文献信息

• An Alternative Route to the Preparation of (3′ → 5′) Methylene Acetal Linked Di- and Trinucleosides
  作者：Peter J. L. M. Quaedflieg、Cornelis M. Timmers、Gijs A. van der Marel、Esther Kuyl-Yeheskiely、Jacques H. van Boom

  DOI：10.1055/s-1993-25915

  日期：——

  Reaction of deoxynucleoside 3′-O-(methylthiomethyl) acetals 1 with N-iodosuccinimide (NIS) and dibutyl phosphate furnished the corresponding 3′-O-(dibutoxyphosphoryloxy)methyl acetals 6. Condensation of the latter with appropriately protected deoxynucleoside acceptors 3, in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf), afforded in most cases the (3′ → 5′) methylene acetal linked d(B1 Î¥ B2) dimers 4. In addition, TMSOTf-promoted coupling of donor 6 (B1 = CBz) with 3′-O-(methylthiomethyl)thymidine (8) yielded dimer 9. Reaction of 9 with NIS and dibutyl phosphate gave dimer 10, which was applied successfully in the TMSOTf-assisted fusion with acceptors 3(B2 = CBz and ABz), to afford the corresponding trimers d(CÎ¥TÎ¥C) 11 and d(CÎ¥TÎ¥A) 12.

  脱氧核苷3′-O-(甲硫基甲基)乙缩醛1与碘代琥珀酰亚胺(NIS)和二丁基磷酸酯反应，生成相应的3′-O-(二丁氧基磷酰氧)甲基乙缩醛6。后者与适当保护的脱氧核苷受体3在三甲基硅基三氟甲磺酸盐(TMSOTf)的存在下缩合，通常得到(3′ → 5′)亚甲基乙缩醛连接的二聚体d(B1 ∧ B2) 4。此外，TMSOTf促进的供体6 (B1 = CBz)与3′-O-(甲硫基甲基)胸苷(8)的偶联反应生成二聚体9。9与NIS和二丁基磷酸酯反应生成二聚体10，成功用于与受体3(B2 = CBz和ABz)的TMSOTf辅助融合，得到相应的三聚体d(C∧T∧C) 11和d(C∧T∧A) 12。
• Chemoenzymatic Synthesis of 3′-<i>O</i>-Acetal-Protected 2′-Deoxynucleosides as Building Blocks for Nucleic Acid Chemistry
  作者：Tatiana Rodríguez-Pérez、Susana Fernández、Saúl Martínez-Montero、Tania González-García、Yogesh S. Sanghvi、Vicente Gotor、Miguel Ferrero

  DOI：10.1002/ejoc.200901428

  日期：2010.3

  , and tetrahydrofuranyl ethers of 2'-deoxynucleosides, which are useful building blocks for nucleic acid chemistry. Enzymatic benzoylation provides an efficient alternative for protecting the 5'-hydroxy group of the parent nucleosides in a regioselective manner. Subsequently, tetra-hydropyranylation and tetrahydrofuranylation of the 2'-deoxynucleosides at the 3'-hydroxy group were accomplished with

  我们开发了一种简单方便的合成策略，用于制备 2'-脱氧核苷的四氢吡喃基、4-甲氧基-四氢吡喃基和四氢呋喃基醚，它们是核酸化学的有用组成部分。酶促苯甲酰化为以区域选择性方式保护母体核苷的 5'-羟基提供了一种有效的替代方法。随后，以对甲苯磺酸、MgBr 2 或樟脑磺酸为催化剂，对3'-羟基上的2'-脱氧核苷进行四氢吡喃化和四氢呋喃化反应。5'-O-苯甲酰基的脱保护提供了 3'-O-缩醛保护的 2'-脱氧核苷。三步法有望实现受保护核苷的大规模合成。
• Study on Disulfur-Backboned Nucleic Acid: Part 1, Efficient Synthesis of 3′,5′-Dithio-2′-Deoxyadenosine
  作者：Changmei Cheng、Hongchao Zheng、Hua Wang、Shanshan Xu、Yufen Zhao

  DOI：10.1055/s-2004-834809

  日期：——

  An efficient procedure is established to synthesize 3',5'-dithio-2'-deoxyadenosine starting from 2'-deoxyadenosine in five steps in 33% overall yield. In this procedure, the key intermediate 9 was synthesized by twice S N 2 reactions with twice 3'-configuration inversions and then it was deprotected to title compound by removing three acyl groups in one pot.

  建立了一个有效的程序来合成 3',5'-二硫-2'-脱氧腺苷，从 2'-脱氧腺苷开始，分五步，总产率为 33%。在该程序中，关键中间体9通过两次3'-构型反转的两次SN 2 反应合成，然后通过在一锅中去除三个酰基将其脱保护为标题化合物。
• 3'-(2')-amino or thiol-modified, fluorescent dye-coupled
  申请人：Hoechst Aktiengesellschaft

  公开号：US05659025A1

  公开（公告）日：1997-08-19

  The OH group located in the 3' and/or 2' position of a nucleoside, nucleotide or oligonucleotide is derivatized to an amino or thiol group and subsequently a fluorescent dye is coupled thereto. The resulting 3'- and/or 2'-amino- and thiol-modified nucleosides, nucleotides and oligonucleotides can then be used for the synthesis of complementary strands in the presence of a template strand or of oligonucleotides and for the detection of genetic material. They have the advantage that the fluorescent label need no longer be attached to the 5' end of the oligonucleotide or to the nucleobase, and thus need not be introduced during the chemical synthesis as in labeling techniques hitherto known, while the known and conventional methods have the disadvantage that only a few polymerases can be employed for the synthesis, the acceptance of the triphosphates by the polymerases diminishes and, moreover, a large substrate excess is necessary.

  位于核苷酸，核苷酸或寡核苷酸的3'和/或2'位置的OH基团被衍生为氨基或巯基，随后荧光染料与其偶联。由此产生的3'-和/或2'-氨基和巯基修饰的核苷酸，核苷酸和寡核苷酸可以在模板链或寡核苷酸存在下用于合成互补链和检测遗传物质。它们的优点是，荧光标记不再需要连接到寡核苷酸的5'端或核碱基上，因此不需要像已知的标记技术中那样在化学合成过程中引入，而已知的传统方法的缺点是只有少数聚合酶可以用于合成，聚合酶对三磷酸盐的接受度降低，此外，需要大量底物过剩。
• 3'-(2')-amimo- or thiol-modified, fluorescent dye-coupled nucleosides,
  申请人：Hoechst Aktiengesellschaft

  公开号：US05668269A1

  公开（公告）日：1997-09-16

  3'-(2')-Amino- or thiol-modified, fluorescent dye-coupled nucleosides, nucleotides and oligonucleotides, and a process for the preparation and the use thereof. The OH group located in the 3' and/or 2' position of a nucleoside, nucleotide or oligonucleotide is derivatized to an amino or thiol group and subsequently a fluorescent dye is coupled thereto. The resulting 3'- and/or 2'-amino- and thiol-modified nucleosides, nucleotides and oligonucleotides can then be used for the synthesis of complementary strands in the presence of a template strand or of oligonucleotides and for the detection of genetic material. They have the advantage that the fluorescent label need no longer be attached to the 5' end of the oligonucleotide or to the nucleobase, and thus need not be introduced during the chemical synthesis as in labeling techniques hitherto known, while the known and conventional methods have the disadvantage that only a few polymerases can be employed for the synthesis, the acceptance of the triphosphates by the polymerases diminishes and, moreover, a large substrate excess is necessary.

  3'-(2')-氨基或巯基修饰的荧光染料偶联核苷、核苷酸和寡核苷酸，以及其制备和使用的方法。将位于核苷、核苷酸或寡核苷酸的3'和/或2'位置上的OH基团衍生成氨基或巯基，然后将荧光染料偶联到其上。得到的3'-和/或2'-氨基和巯基修饰的核苷、核苷酸和寡核苷酸可以在模板链或寡核苷酸存在的情况下用于合成互补链和检测遗传物质。它们的优点是荧光标记不再需要附加到寡核苷酸的5'端或核碱基上，因此不像迄今已知的标记技术中那样需要在化学合成过程中引入，而已知的传统方法的缺点是只有少数聚合酶可用于合成，聚合酶对三磷酸盐的接受能力降低，此外还需要大量的底物过量。