3-O-benzyloxymethyl-1,2,5,6-di-O-isopropylidene-α-D-allofuranose | 1204744-76-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-benzyloxymethyl-1,2,5,6-di-O-isopropylidene-α-D-allofuranose
• CAS: 1204744-76-2
• 化学式: C₂₀H₂₈O₇
• 分子量: 380.438
• InChiKey: ROBFMGLGEGXILZ-DUQPFJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-O-benzyloxymethyl-1,2,5,6-di-O-isopropylidene-α-D-allofuranose 在 水 、 溶剂黄146 作用下， 反应 0.5h， 以80%的产率得到3-O-benzyloxymethyl-1,2-O-isopropylidene-α-D-allofuranose
  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：

  苄基氯甲基醚 、 1,2:5,6-二异亚丙基-alpha-D-异呋喃糖 在 N,N-二异丙基乙胺 、 水 作用下， 以 二氯甲烷 为溶剂， 以87.4%的产率得到3-O-benzyloxymethyl-1,2,5,6-di-O-isopropylidene-α-D-allofuranose
  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.