N3-pivaloyloxymethyl-2'-O-[N-(2,3-diacetoxypropyl)aminocarbonyl]methyluridine | 863446-49-5

• 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: N3-pivaloyloxymethyl-2'-O-[N-(2,3-diacetoxypropyl)aminocarbonyl]methyluridine
• 英文别名: N³-pivaloyloxymethyl-2'-O-[N-(2,3-diacetoxypropyl)aminocarbonyl]methyluridine；2'-O-[2-(2,3-diacetoxypropyl)amino-2-oxoethyl]-N³-pivaloyloxymethyluridine
• CAS: 863446-49-5
• 化学式: C₂₄H₃₅N₃O₁₃
• 分子量: 573.554
• InChiKey: GYROCCSUUJGXSS-ITKDDASESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  40.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  210.92
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  N3-pivaloyloxymethyl-2'-O-[N-(2,3-diacetoxypropyl)aminocarbonyl]methyluridine 在 吡啶 、 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 2'-O-[2-(2,3-diacetoxypropyl)amino-2-oxoethyl]-3'-O-(N,N-diisopropylamino-2-cyanoethoxyphosphinyl)-5'-O-(4,4'-dimethoxytrityl)-N³-pivaloyloxymethyluridine
  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
• 作为产物：
  描述：

  2'-O-[2-(2,3-diacetoxypropyl)amino-2-oxoethyl]-N3-pivaloyloxymethyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine 在 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 生成 N3-pivaloyloxymethyl-2'-O-[N-(2,3-diacetoxypropyl)aminocarbonyl]methyluridine
  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