N-{1-[(2R,3R,3aR,9aR)-3-(2,3-Dihydroxy-propoxy)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide | 176747-26-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-{1-[(2R,3R,3aR,9aR)-3-(2,3-Dihydroxy-propoxy)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide
• CAS: 176747-26-5
• 化学式: C₃₁H₄₉N₃O₉Si₂
• 分子量: 663.916
• InChiKey: DIYBCZRSGVLFKQ-FYKBAZAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  45.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  150.6
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-{1-[(2R,3R,3aR,9aR)-3-(2,3-Dihydroxy-propoxy)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 在 吡啶 、 sodium tetrahydroborate 、 sodium periodate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 94.5h， 生成 2-[[(6aR,8R,9R,9aR)-8-(4-benzamido-2-oxopyrimidin-1-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl]oxy]ethyl methanesulfonate
  参考文献：
  名称：

  Design, Synthesis, and Analysis of Yeast tRNA^Phe Analogs Possessing Intra- and Interhelical Disulfide Cross-Links

  摘要：

  Disulfide cross-links have been site-specifically incorporated into unmodified yeast tRNA(Phe) by total chemical synthesis. One cross-link is between positions 1 and 72 in the amino-acid acceptor stem, and it was prepared by replacing G1 and C72 with N-3-(thioethyl)uridine. A second cross-link is in the central D-region of yeast tRNA(Phe) between 11 and 25, and it was synthesized by replacing C11 and C25 with 2'-O-alkylthiol modified cytosine residues. Air oxidation to form the cross-link at both sites occurs in 12 h and is nearly quantitative. Analysis of the crosslinked products by native and denaturing PAGE along with Pb(II) cleavage experiments demonstrates that the crosslinked molecules are monomeric and suggests that the disulfide bridges do not significantly alter the structure of the modified tRNAs relative to the parent sequence. The finding that cross-link formation between thiol-derivatized residues correlates with the position of these groups in the crystal structure of native yeast tRNA(Phe) that the modifications apparently do not perturb native structure suggests that this methodology should be applicable to the study of RNA structure, dynamics, and folding.

  DOI：

  10.1021/ja960091t
• 作为产物：
  描述：

  N-[1-((2R,3R,3aR,9aR)-3-Allyloxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 丙酮 为溶剂， 反应 2.5h， 以90%的产率得到N-{1-[(2R,3R,3aR,9aR)-3-(2,3-Dihydroxy-propoxy)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide
  参考文献：
  名称：

  Design, Synthesis, and Analysis of Yeast tRNA^Phe Analogs Possessing Intra- and Interhelical Disulfide Cross-Links

  摘要：

  Disulfide cross-links have been site-specifically incorporated into unmodified yeast tRNA(Phe) by total chemical synthesis. One cross-link is between positions 1 and 72 in the amino-acid acceptor stem, and it was prepared by replacing G1 and C72 with N-3-(thioethyl)uridine. A second cross-link is in the central D-region of yeast tRNA(Phe) between 11 and 25, and it was synthesized by replacing C11 and C25 with 2'-O-alkylthiol modified cytosine residues. Air oxidation to form the cross-link at both sites occurs in 12 h and is nearly quantitative. Analysis of the crosslinked products by native and denaturing PAGE along with Pb(II) cleavage experiments demonstrates that the crosslinked molecules are monomeric and suggests that the disulfide bridges do not significantly alter the structure of the modified tRNAs relative to the parent sequence. The finding that cross-link formation between thiol-derivatized residues correlates with the position of these groups in the crystal structure of native yeast tRNA(Phe) that the modifications apparently do not perturb native structure suggests that this methodology should be applicable to the study of RNA structure, dynamics, and folding.

  DOI：

  10.1021/ja960091t

文献信息

• Synthesis of DNA conjugates by solid-phase fragment condensation via aldehyde–nucleophile coupling
  作者：Timofei S. Zatsepin、Dmitry A. Stetsenko、Michael J. Gait、Tatiana S. Oretskaya

  DOI：10.1016/j.tetlet.2005.03.056

  日期：2005.5

  Oligodeoxyribonucletides were synthesized that contain a novel nucleoside, 2'-O-(2,3-dihydroxypropyl)cytidine. Its 2'diol group was blocked by an allyloxycarbonyl protecting group. Selective deprotection of diol group(s) of the support-immobilized blocked oligodcoxyribonucleotide by Pd(0) followed by periodate oxidation resulted in generation of the 2'-aldehyde group(s) on solid-phase. The modified oligonucleotides were used to prepare a number of conjugates with acridine, biotin and N-modified laminin peptides by oxime, hydrazone and hydrazine formation. The method may be applicable to the synthesis of oligonucleotide-peptide conjugates. (c) 2005 Elsevier Ltd. All rights reserved.