1-[3'-Deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil | 175355-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-[3'-Deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil
• 英文别名: DMT(-6)3-deoxy-D-eryHex2ulof(b)-uracil-1-yl；1-[(2S,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-2-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 175355-17-6
• 化学式: C₃₁H₃₂N₂O₈
• 分子量: 560.604
• InChiKey: UTRVNAYUZBCVQX-DURBRWELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  127
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[3'-Deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil 在 palladium hydroxide - carbon 吡啶 、 sodium hydroxide 、 氢气 、 sodium hydride 、 戴斯-马丁氧化剂 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 77.5h， 生成 (1S,5R,6S)-6-benzyloxy-5-methanesulfonyloxymethyl-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane
  参考文献：
  名称：

  新型双环核苷类似物（1S，5S，6S）-6-羟基-5-羟甲基-1-（尿嘧啶-1-基）-3,8-二氧杂双环[3.2.1]辛烷：合成并掺入寡脱氧核苷酸。

  摘要：

  新型双环核苷（1S，5S，6S）-6-羟基-5-羟甲基-1-（尿嘧啶-1-基）-3,8-二氧杂双环[3.2.1]辛烷[2'-脱氧-1'-由已知的1-（3'-脱氧-β-D-psico呋喃糖基）合成预期被限制为O4'-内呋喃糖构象的C，4'-C-（2-氧杂丙烷）尿苷]（15）尿嘧啶5。使用标准方法成功地将15的亚磷酰胺衍生物掺入到寡脱氧核苷酸中，热变性研究表明，针对互补DNA和RNA的每种修饰，双链体稳定性分别适度降低-2.1和-1.5℃。

  DOI：

  10.1021/jo015664l
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 1-(3'-deoxy-β-D-psicofuranosyl)uracil 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 以37%的产率得到1-[3'-Deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil
  参考文献：
  名称：

  Synthesis and anti-HIV-1 activity of novel bicyclic nucleoside analogues restricted to an S-type conformation

  摘要：

  (1S,3R,4S)-3-羟甲基-1-(尿嘧啶-1-基)-2,5-二氧杂环[2.2.1]庚烷 9 和相应的胞嘧啶衍生物 10 是具有新型双环核苷结构 3 的核苷类似物，由已知的 1-(3′-脱氧-β-D-二十呋喃糖基)尿嘧啶 4 通过几个步骤合成。NOE 实验验证了双环核苷仅限于预期的 S 型呋喃糖构象，而核碱基则处于反构象。事实证明，这两种核苷在 MT-4 细胞中都没有抗 HIV 活性，这进一步证实了一个假设，即核苷类似物中呋喃糖环的构象灵活性是获得细胞内 5′-三磷酸化和抑制 HIV-1 逆转录酶的必要条件。

  DOI：

  10.1039/b004774k

文献信息

• Building Blocks for Ribozyme Mimics:  Conjugates of Terpyridine and Bipyridine with Nucleosides
  作者：James K. Bashkin、Jin Xie、Andrew T. Daniher、UmaShanker Sampath、Jeffrey L.-F. Kao

  DOI：10.1021/jo9518213

  日期：1996.1.1

  The incorporation of the 2,2':6',2 ''-terpyridyl (terpy) complex of Cu(II) into a deoxyoligonucleotide has led to a functional mimic of ribozymes. The resulting mimic can cleave target RNA in a sequence-directed manner by a hydrolytic mechanism. Here we describe the synthesis and characterization of four modified nucleoside phosphoramidite reagents (7, 10, 14, and 18) that contain pendant 2,2'-bipyridine or terpy ligands. The ligands are attached either to the nucleobase (7, 10) or to the sugar (14, 18). Nucleobase modification was carried out at the C-5 position of 2'-deoxyuridine (dU). One route to sugar modification was performed by synthesis of 18, a 1'-functionalized analog of dU based on 1-[3-deoxy-beta-D-psicofuranosyl]uracil. Another route to sugar functionaliztion resulted in 14, a 2'-O-alkyl derivative of adenosine. These modified nucleosides are building blocks for ribozyme mimics. They are designed to deliver hydrolytically active metal complexes across either the major groove (7, 10) or the minor groove (14, 18) of an RNA/DNA duplex.
• Novel Bicyclic Nucleoside Analogue (1<i>S</i>,5<i>S</i>,6<i>S</i>)-6- Hydroxy-5-hydroxymethyl-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane:  Synthesis and Incorporation into Oligodeoxynucleotides
  作者：Lisbet Kværnø、Jesper Wengel

  DOI：10.1021/jo015664l

  日期：2001.8.1

  [2'-deoxy-1'-C,4'-C-(2-oxapropano)uridine] (15), expected to be restricted into an O4'-endo furanose conformation, was synthesized from the known 1-(3'-deoxy-beta-D-psicofuranosyl)uracil 5. The phosphoramidite derivative of 15 was successfully incorporated into oligodeoxynucleotides using standard methods, and thermal denaturation studies showed moderate decreases in duplex stabilities of -2.1 and -1

  新型双环核苷（1S，5S，6S）-6-羟基-5-羟甲基-1-（尿嘧啶-1-基）-3,8-二氧杂双环[3.2.1]辛烷[2'-脱氧-1'-由已知的1-（3'-脱氧-β-D-psico呋喃糖基）合成预期被限制为O4'-内呋喃糖构象的C，4'-C-（2-氧杂丙烷）尿苷]（15）尿嘧啶5。使用标准方法成功地将15的亚磷酰胺衍生物掺入到寡脱氧核苷酸中，热变性研究表明，针对互补DNA和RNA的每种修饰，双链体稳定性分别适度降低-2.1和-1.5℃。
• Synthesis and anti-HIV-1 activity of novel bicyclic nucleoside analogues restricted to an S-type conformation
  作者：Lisbet Kvrnø、Claus Nielsen、Richard H. Wightman

  DOI：10.1039/b004774k

  日期：——

  (1S,3R,4S)-3-Hydroxymethyl-1-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 9 and the corresponding cytosine derivative 10, nucleoside analogues with a novel bicyclic nucleoside structure 3, were synthesized in a few steps from the known 1-(3′-deoxy-β-D-psicofuranosyl)uracil 4. NOE experiments verified the bicyclic nucleosides to be restricted to the expected S-type furanose conformation while the nucleobase is in an anti-conformation. Both nucleosides proved to be devoid of anti-HIV activity in MT-4 cells, which further supports the hypothesis that conformational flexibility of the furanose ring in a nucleoside analogue is necessary to obtain both intracellular 5′-triphosphorylation and inhibition of HIV-1 reverse transcriptase.

  (1S,3R,4S)-3-羟甲基-1-(尿嘧啶-1-基)-2,5-二氧杂环[2.2.1]庚烷 9 和相应的胞嘧啶衍生物 10 是具有新型双环核苷结构 3 的核苷类似物，由已知的 1-(3′-脱氧-β-D-二十呋喃糖基)尿嘧啶 4 通过几个步骤合成。NOE 实验验证了双环核苷仅限于预期的 S 型呋喃糖构象，而核碱基则处于反构象。事实证明，这两种核苷在 MT-4 细胞中都没有抗 HIV 活性，这进一步证实了一个假设，即核苷类似物中呋喃糖环的构象灵活性是获得细胞内 5′-三磷酸化和抑制 HIV-1 逆转录酶的必要条件。