3-N-benzoyl-1-(3',5'-O,O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl)uracil | 809290-41-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-N-benzoyl-1-(3',5'-O,O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl)uracil
• CAS: 809290-41-3
• 化学式: C₂₈H₄₂N₂O₈Si₂
• 分子量: 590.821
• InChiKey: SPZRITYJFHGMOE-POHJQOBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  40.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  118.22
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3-N-benzoyl-1-(3',5'-O,O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl)uracil 在 咪唑 、 tris-(dibenzylideneacetone)dipalladium(0) 、 四丁基氟化铵 、 溶剂黄146 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.58h， 生成 2'-O-allyl-3'-O-tert-butyldimethylsilyl-araU
  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：

  苯甲酰氯 、 1-[(6aR,8R,9S,9aS)-9-hydroxy-2,2,4,4-tetraisopropyl-tetrahydro-6H-furo[3,2-f][1,3,5,2,4] trioxadisilocin-8-yl]-3H-pyrimidine-2,4-dione 在 三甲基氯硅烷 、 三乙胺 、 吡啶 、 N,N-二异丙基乙胺 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 19.17h， 以81%的产率得到3-N-benzoyl-1-(3',5'-O,O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl)uracil
  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