2'-O-allyl-5'-O-(tert-butyldimethylsilyl)uridine | 809290-39-9

• 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: 2'-O-allyl-5'-O-(tert-butyldimethylsilyl)uridine
• 英文别名: allyl(-2)[TBDMS(-5)]Ribf(b)-uracil-1-yl；1-[(2R,3R,4R,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxy-3-prop-2-enoxyoxolan-2-yl]pyrimidine-2,4-dione
• CAS: 809290-39-9
• 化学式: C₁₈H₃₀N₂O₆Si
• 分子量: 398.531
• InChiKey: FLISZJIXFABNON-DTZQCDIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2'-O-allyl-5'-O-(tert-butyldimethylsilyl)uridine 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 4.25h， 生成 allyl 2'-O-allyl-5'-O-(tert-butyldimethylsilyl)uridin-3'-yl 3'-O-(ter-butyldimethylsilyl)thymidin-5'-yl phosphate
  参考文献：
  名称：

  通过闭环复分解合成具有2'-C磷酸连接的二核苷酸

  摘要：

  制备了具有烯烃2'-修饰的四个不同的核苷。2′- C-亚甲基，2′ - C-（丙烯-1-基），2′- C-烯丙基和2′- O-烯丙基尿苷。将它们掺入具有烯丙基磷酸酯或乙烯基膦酸酯键的二核苷酸中。因此，研究了六种不同的二核苷酸作为RCM反应的底物，并从其中的四个中获得了2'-C和3-6个原子的磷之间有连接的环状二核苷酸。

  DOI：

  10.1016/j.tet.2005.10.074
• 作为产物：
  描述：

  N³-benzoyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 在 吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 四丁基氟化铵 、 silver nitrate 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 为溶剂， 反应 27.33h， 生成 2'-O-allyl-5'-O-(tert-butyldimethylsilyl)uridine
  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

文献信息

• Synthesis of dinucleotides with 2′-C to phosphate connections by ring-closing metathesis
  作者：Philip Børsting、Mikkel S. Christensen、Signe I. Steffansen、Poul Nielsen

  DOI：10.1016/j.tet.2005.10.074

  日期：2006.2

  nucleosides with olefinic 2′-modifications were prepared; 2′-C-methylene, 2′-C-(propen-1-yl), 2′-C-allyl and 2′-O-allyl uridines, respectively. These were incorporated into dinucleotides with allyl phosphate or vinyl phosphonate linkages. Hence, six different dinucleotides were studied as substrates for RCM reactions, and from four of these, cyclic dinucleotides with connections between 2′-C and phosphorus

  制备了具有烯烃2'-修饰的四个不同的核苷。2′- C-亚甲基，2′ - C-（丙烯-1-基），2′- C-烯丙基和2′- O-烯丙基尿苷。将它们掺入具有烯丙基磷酸酯或乙烯基膦酸酯键的二核苷酸中。因此，研究了六种不同的二核苷酸作为RCM反应的底物，并从其中的四个中获得了2'-C和3-6个原子的磷之间有连接的环状二核苷酸。
• 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.