5-azido-3,5-dideoxy-3-[2-(tert-butyldiphenylsilyloxy)-ethyl]-1,2-O-isopropylidene-α-D-ribofuranose | 1237761-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azido-3,5-dideoxy-3-[2-(tert-butyldiphenylsilyloxy)-ethyl]-1,2-O-isopropylidene-α-D-ribofuranose
• 英文别名: 2-[(3aR,5S,6R,6aR)-5-(azidomethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]ethoxy-tert-butyl-diphenylsilane
• CAS: 1237761-83-9
• 化学式: C₂₆H₃₅N₃O₄Si
• 分子量: 481.667
• InChiKey: LMNQUYBYNVLCGS-MOUTVQLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-azido-3,5-dideoxy-3-[2-(tert-butyldiphenylsilyloxy)-ethyl]-1,2-O-isopropylidene-α-D-ribofuranose 在 三氯化硼 、 碳酸氢钠 作用下， 以 hexanes 、 二氯甲烷 、 水 为溶剂， 反应 0.5h， 以0.309 g的产率得到5-azido-3,5-dideoxy-3-[2-(tert-butyldiphenylsilyloxy)-ethyl]-D-ribofuranose
  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
• 作为产物：
  描述：

  5-azido-3,5-dideoxy-3-(2-hydroxyethyl)-1,2-O-isopropylidene-α-D-ribofuranose 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以79%的产率得到5-azido-3,5-dideoxy-3-[2-(tert-butyldiphenylsilyloxy)-ethyl]-1,2-O-isopropylidene-α-D-ribofuranose
  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

文献信息

• Monomers for preparation of amide linked RNA: synthesis of C3′-homologated nucleoside amino acids from d-xylose
  作者：Paul Tanui、Martin Kullberg、Ni Song、Yashodhan Chivate、Eriks Rozners

  DOI：10.1016/j.tet.2010.04.110

  日期：2010.7

  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.