5-deoxy-1,2-O-isopropylidene-5-ethoxycarbonylmethyl-α-D-ribofuranose | 1204744-80-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-deoxy-1,2-O-isopropylidene-5-ethoxycarbonylmethyl-α-D-ribofuranose
• 英文别名: ethyl 3-[(3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propanoate
• CAS: 1204744-80-8
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: HJNHADRSSAHDCO-QCNRFFRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-deoxy-1,2-O-isopropylidene-5-ethoxycarbonylmethyl-α-D-ribofuranose 、 溴甲苯 在 sodium hydride 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以69.9%的产率得到3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-ethoxycarbonylmethyl-α-D-ribofuranose
  参考文献：
  名称：

  Synthesis of 5′-deoxy-5′-ethoxycarbonylmethyl nucleosides, the precursors of oligonucleotides with the amide internucleoside bond C3′-NH-C(O)-CH2-C5′

  摘要：

  A method for the synthesis of 5'-deoxy-5'-ethoxycarbonylmethyl nucleosides has been developed. 3-O-benzyloxymethyl-1,2-O-isopropylidene-alpha-D-allofuranose was oxidized by sodium periodate to form a 5'-aldo derivative, which was converted by the reaction with triethylphosphonoacetate in the presence of sodium hydride into a 5-deoxy-5-ethoxycarbonylmethylene derivative. The hydration of the unsaturated compound gave 5-deoxy-5-ethoxycarbonylmethyl-1,2-O-isopropylidene-alpha-D-ribofuranose. After the benzylation of 3-hydroxyl, the removal of the isopropylidene group by heating with acetic acid, and the subsequent acetylation, 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-ethoxycarbonylmethyl-D-ribofuranose was obtained, which reacted with persilylated nucleic acid bases to form 5'-deoxy-5'-ethoxycarbonylmethyl nucleosides.

  DOI：

  10.1134/s1068162009050082
• 作为产物：
  描述：

  3-O-benzyloxymethyl-5-deoxy-1,2-O-isopropylidene-5-ethoxycarbonylmethylene-α-D-ribofuranose 在 Pearlman's catalist 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以98.7%的产率得到5-deoxy-1,2-O-isopropylidene-5-ethoxycarbonylmethyl-α-D-ribofuranose
  参考文献：
  名称：

  Synthesis of 5′-deoxy-5′-ethoxycarbonylmethyl nucleosides, the precursors of oligonucleotides with the amide internucleoside bond C3′-NH-C(O)-CH2-C5′

  摘要：

  A method for the synthesis of 5'-deoxy-5'-ethoxycarbonylmethyl nucleosides has been developed. 3-O-benzyloxymethyl-1,2-O-isopropylidene-alpha-D-allofuranose was oxidized by sodium periodate to form a 5'-aldo derivative, which was converted by the reaction with triethylphosphonoacetate in the presence of sodium hydride into a 5-deoxy-5-ethoxycarbonylmethylene derivative. The hydration of the unsaturated compound gave 5-deoxy-5-ethoxycarbonylmethyl-1,2-O-isopropylidene-alpha-D-ribofuranose. After the benzylation of 3-hydroxyl, the removal of the isopropylidene group by heating with acetic acid, and the subsequent acetylation, 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-ethoxycarbonylmethyl-D-ribofuranose was obtained, which reacted with persilylated nucleic acid bases to form 5'-deoxy-5'-ethoxycarbonylmethyl nucleosides.

  DOI：

  10.1134/s1068162009050082

文献信息

• Synthesis of 5′-deoxy-5′-ethoxycarbonylmethyl nucleosides, the precursors of oligonucleotides with the amide internucleoside bond C3′-NH-C(O)-CH2-C5′
  作者：A. M. Varizhuk、S. V. Kochetkova、N. A. Kolganova、E. N. Timofeev、V. L. Florent’ev

  DOI：10.1134/s1068162009050082

  日期：2009.9

  A method for the synthesis of 5'-deoxy-5'-ethoxycarbonylmethyl nucleosides has been developed. 3-O-benzyloxymethyl-1,2-O-isopropylidene-alpha-D-allofuranose was oxidized by sodium periodate to form a 5'-aldo derivative, which was converted by the reaction with triethylphosphonoacetate in the presence of sodium hydride into a 5-deoxy-5-ethoxycarbonylmethylene derivative. The hydration of the unsaturated compound gave 5-deoxy-5-ethoxycarbonylmethyl-1,2-O-isopropylidene-alpha-D-ribofuranose. After the benzylation of 3-hydroxyl, the removal of the isopropylidene group by heating with acetic acid, and the subsequent acetylation, 1,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-ethoxycarbonylmethyl-D-ribofuranose was obtained, which reacted with persilylated nucleic acid bases to form 5'-deoxy-5'-ethoxycarbonylmethyl nucleosides.