5-allyl-3'-O-tert-butyldimethylsilyl-2'-deoxyuridine | 492452-95-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-allyl-3'-O-tert-butyldimethylsilyl-2'-deoxyuridine
• 英文别名: 3'-O-[tert-Butyl(dimethyl)silyl]-2'-deoxy-5-prop-2-en-1-yluridine；1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(hydroxymethyl)oxolan-2-yl]-5-prop-2-enylpyrimidine-2,4-dione
• CAS: 492452-95-6
• 化学式: C₁₈H₃₀N₂O₅Si
• 分子量: 382.532
• InChiKey: XTDZFDYAGDZPKU-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-allyl-3'-O-tert-butyldimethylsilyl-2'-deoxyuridine 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 4.0h， 生成 3-[[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2,4-dioxo-5-prop-2-enylpyrimidin-1-yl)oxolan-2-yl]methoxy-[(2R,3R,4R,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)-4-prop-2-enoxyoxolan-3-yl]oxy-oxidophosphaniumyl]oxypropanenitrile
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tet.2004.09.023
• 作为产物：
  描述：

  盐酸土霉素兽药 在 吡啶 、 对甲苯磺酸 、 silver nitrate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 5-allyl-3'-O-tert-butyldimethylsilyl-2'-deoxyuridine
  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

• Tandem ring-closing metathesis and hydrogenation towards cyclic dinucleotides
  作者：Philip Børsting、Poul Nielsen

  DOI：10.1039/b206560f

  日期：——

  Cyclic dinucleotides containing a butylene nucleobase–phophotriester connection are synthesised by a tandem ring-closing metathesis and hydrogenation reaction.

  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。
• 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.