2'-O-acetyl-3',5'-dideoxy-3'-carboxymethyl-5'-(4-monomethoxytrityl)amino-uridine triethylammonium salt | 1237761-88-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2'-O-acetyl-3',5'-dideoxy-3'-carboxymethyl-5'-(4-monomethoxytrityl)amino-uridine triethylammonium salt
• CAS: 1237761-88-4
• 化学式: C₆H₁₅N*C₃₃H₃₃N₃O₈
• 分子量: 700.832
• InChiKey: VKWMTBAVWJAPCJ-AXPJTTQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  51.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  152.19
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  2-[(2S,3R,4R,5R)-4-acetyloxy-2-(aminomethyl)-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl]acetic acid 、 三乙基碳酸氢铵缓冲液 、 4-甲氧基三苯基氯甲烷 在 吡啶 作用下， 以 水 为溶剂， 以362 mg的产率得到2'-O-acetyl-3',5'-dideoxy-3'-carboxymethyl-5'-(4-monomethoxytrityl)amino-uridine triethylammonium salt
  参考文献：
  名称：

  Monomers for preparation of amide linked RNA: synthesis of C3′-homologated nucleoside amino acids from d-xylose

  摘要：

  Amides as neutral and hydrophobic internucleoside linkages in RNA are highly interesting modifications for RNA interference. However, testing amides in siRNAs is hampered by the shortage of efficient methods to synthesize the monomeric building blocks, the nucleoside amino acid equivalents. This paper reports an efficient synthesis of protected ribonucleoside 5'-amino 3'-carboxylic acids from D-xylose in 14 steps 7% overall yield. The key features that ensure efficiency and ease of operations are chemo-selective reduction of the ester and minimization of protecting group manipulation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.110