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