2'-O-allyl-5'-O-(tert-butyldimethylsilyl)uridine-3'-O-{(N,N-diisopropyl)-(2-cyanoethyl)phosphoramidite} | 809290-40-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 2'-O-allyl-5'-O-(tert-butyldimethylsilyl)uridine-3'-O-{(N,N-diisopropyl)-(2-cyanoethyl)phosphoramidite}
• 英文别名: allyl(-2)[N(iPr)2P(OCH2CH2CN)(-3)][TBDMS(-5)]Ribf(b)-uracil-1-yl；3-[[(2R,3R,4R,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)-4-prop-2-enoxyoxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• CAS: 809290-40-2
• 化学式: C₂₇H₄₇N₄O₇PSi
• 分子量: 598.752
• InChiKey: RUMMUJJXHDBECJ-KLPJVMJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2'-O-allyl-5'-O-(tert-butyldimethylsilyl)uridine-3'-O-{(N,N-diisopropyl)-(2-cyanoethyl)phosphoramidite} 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：

  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 、 N,N-二异丙基乙胺 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 33.83h， 生成 2'-O-allyl-5'-O-(tert-butyldimethylsilyl)uridine-3'-O-{(N,N-diisopropyl)-(2-cyanoethyl)phosphoramidite}
  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

• 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.