(2R,4S,5R)-4-Hydroxy-8-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-8-oxo-7,9,19-trioxa-1,16-diaza-8λ⁵-phospha-tricyclo[12.3.1.1^2,5]nonadec-14(18)-ene-15,17-dione | 492453-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (2R,4S,5R)-4-Hydroxy-8-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-8-oxo-7,9,19-trioxa-1,16-diaza-8λ⁵-phospha-tricyclo[12.3.1.1^2,5]nonadec-14(18)-ene-15,17-dione
• 英文别名: (2R,4S,5R)-4-hydroxy-8-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-8-oxo-7,9,19-trioxa-1,16-diaza-8λ5-phosphatricyclo[12.3.1.12,5]nonadec-14(18)-ene-15,17-dione
• CAS: 492453-06-2
• 化学式: C₂₃H₃₁N₄O₁₂P
• 分子量: 586.492
• InChiKey: GRRZJDRUIWIJRN-IXYGFHQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.81
• 重原子数：
  40.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  213.4
• 氢给体数：
  4.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R)-4-Hydroxy-8-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-8-oxo-7,9,19-trioxa-1,16-diaza-8λ⁵-phospha-tricyclo[12.3.1.1^2,5]nonadec-14(18)-ene-15,17-dione 在 ammonium hydroxide 作用下， 反应 120.0h， 以100%的产率得到Phosphoric acid (2R,3S,5R)-5-[5-(4-amino-butyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Tandem ring-closing metathesis and hydrogenation towards cyclic dinucleotides

  摘要：

  含有丁烯核碱基-磷酸三酯连接的环状二核苷酸是通过串联闭环复分解和氢化反应合成的。

  DOI：

  10.1039/b206560f
• 作为产物：
  描述：

  5-allyl-3'-O-tert-butyldimethylsilyl-2'-deoxyuridine 在 四氮唑 、 叔丁基过氧化氢 、 Grubbs catalyst first generation 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 40.0~50.0 ℃ 、6.89 MPa 条件下， 生成 (2R,4S,5R)-4-Hydroxy-8-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-8-oxo-7,9,19-trioxa-1,16-diaza-8λ⁵-phospha-tricyclo[12.3.1.1^2,5]nonadec-14(18)-ene-15,17-dione
  参考文献：
  名称：

  Tandem ring-closing metathesis and hydrogenation towards cyclic dinucleotides

  摘要：

  含有丁烯核碱基-磷酸三酯连接的环状二核苷酸是通过串联闭环复分解和氢化反应合成的。

  DOI：

  10.1039/b206560f

文献信息

• Dinucleotides containing two allyl groups by combinations of allyl phosphotriesters, 5-allyl-, 2′-O-allyl- and 2′-arabino-O-allyl uridine derivatives as substrates for ring-closing metathesis
  作者：Philip Børsting、Morten Freitag、Poul Nielsen

  DOI：10.1016/j.tet.2004.09.023

  日期：2004.11

  Five different dinucleotides, each containing two allyl groups in various positions, were prepared and studied as substrates for ring-closing metathesis reactions. These dinucleotides were designed from appropriate nucleoside building blocks combining four different positions for the allyl group; the allyl phosphotriester linkage, 5-allyl-2' -deoxyuridine, and ribo- as well as arabino-configured 2'-O-allyluridine. Thus, convenient procedures for these building blocks were developed. From the dinucleotides, two new cyclic nucleotide structures were obtained; one connecting two adjacent nucleobase moieties and the other forming an unsaturated four-carbon linkage between the phosphate moiety and the adjacent pyrimidine nucleobase. The latter cyclic dinucleotide was also prepared with a saturated four-carbon linkage using a tandem ring-closing metathesis-hydrogenation procedure. This compound was found to be significantly more stable towards a nucleophilic ring-opening than its unsaturated counterpart. (C) 2004 Elsevier Ltd. All rights reserved.
• 10.1081/ncn-120022820
  作者：Borsting, Philip、Nielsen, Poul

  DOI：10.1081/ncn-120022820

  日期：——