2'-O-(2-benzyloxy-2-oxoethyl)-N³-pivaloyloxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine | 863446-47-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-O-(2-benzyloxy-2-oxoethyl)-N³-pivaloyloxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine
• 英文别名: 2'-O-benzyloxycarbonylmethyl-3-pivaloyoxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine；[3-[(6aR,8R,9R,9aR)-9-(2-oxo-2-phenylmethoxyethoxy)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-2,6-dioxopyrimidin-1-yl]methyl 2,2-dimethylpropanoate
• CAS: 863446-47-3
• 化学式: C₃₆H₅₆N₂O₁₁Si₂
• 分子量: 749.018
• InChiKey: RKKACXRUJNSXOH-LXSYHGDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  51.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  142.75
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2'-O-(2-benzyloxy-2-oxoethyl)-N³-pivaloyloxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine 在 吡啶 作用下， 生成 2'-O-[2-(2,3-diacetoxypropyl)amino-2-oxoethyl]-N3-pivaloyloxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine
  参考文献：
  名称：

  1,2-Diol and Hydrazide Phosphoramidites for Solid-Phase Synthesis and Chemoselective Ligation of 2′-Modified Oligonucleotides

  摘要：

  The preparation of two novel 2'-O-alkyl phosphoramidites bearing 1,2-diol and hydrazide functions for a chemoselective ligation is described. The former amidite was used to obtain 2'-modified oligodeoxyribonucleotides, which can be later oxidised by NaIO4 to generate 2'-aldehyde oligonucleotides. These were successfully conjugated to acceptor molecules. The latter amidite also showed good coupling yields, but the hydrazide function was demonstrated to be labile under basic deprotection conditions.

  DOI：

  10.1081/ncn-120022969
• 作为产物：
  描述：

  3',5'-O-(1,1,3,3-四异丙基-1,3-二硅氧烷)尿苷 在 四丁基硫酸氢铵 、 sodium carbonate 、 (叔丁基亚氨基)三(吡咯烷)膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 51.0h， 生成 2'-O-(2-benzyloxy-2-oxoethyl)-N³-pivaloyloxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine
  参考文献：
  名称：

  Oligonucleotides containing 2′-O-[2-(2,3-dihydroxypropyl)amino-2-oxoethyl]uridine as suitable precursors of 2′-aldehyde oligonucleotides for chemoselective ligation

  摘要：

  2'-O-[2-(2.3-Diacetoxypropyl)amino-2-oxoethyl]uridine 3'-phosphoramidite was prepared and used in solid-phase-synthesis to obtain oligonucleotides containing a 1,2-diol group. which may then be converted into it 2'-aldehyde group. The oligonucleotides were conjugated efficiently to various Molecules by chemoselective ligation that involves all addition elimination reaction between the 2'-aldehyde group and a suitable nucleophile such as it hydrazine, a O-alkylhydroxylamine or in 1,2-aminothiol. The method was applied Successfully to the conjugation of peptides to oligonucleotides at the T-position, (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.024

文献信息

• Synthesis of oligo-2′-O-methylribonucleotides containing α-amino acid residues in 2′-position
  作者：E. V. Kazanova、E. M. Zubin、V. Kachalova、D. A. Stetsenko、M. J. Gait、T. S. Oretskaya

  DOI：10.1007/s11172-007-0120-2

  日期：2007.4

  Oligo-2′-O-methylribonucleotides containing residues of phenylalanine, histidine, and lysine amides were synthesized with the use of new phosphoramidites of 2′-aminoacid derivatives of uridine.

  利用尿苷2'-氨基酸衍生物的新亚磷酰胺合成了含有苯丙氨酸、组氨酸和赖氨酸酰胺残基的寡-2'-O-甲基核糖核苷酸。