5-O-benzoyl-3-deoxy-3-ethoxycarbonylmethylene-1,2-O-isopropylidene-α-D-ribofuranose | 77772-47-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-O-benzoyl-3-deoxy-3-ethoxycarbonylmethylene-1,2-O-isopropylidene-α-D-ribofuranose
• 英文别名: 5-O-benzoyl-3-ethoxycarbonylmethylene-1,2-O-isopropylidene-α-D-ribofuranose
• CAS: 77772-47-5
• 化学式: C₁₉H₂₂O₇
• 分子量: 362.379
• InChiKey: CNVOZMCACWUXQO-QGPMSJSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-O-benzoyl-3-deoxy-3-ethoxycarbonylmethylene-1,2-O-isopropylidene-α-D-ribofuranose 在 palladium hydroxide on carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 以98%的产率得到((3aR,5S,6R,6aR)-6-(2-ethoxy-2-oxoethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate
  参考文献：
  名称：

  Synthesis of 3′-deoxy-3′-carboxymethylnucleosides, precursors of oligonucleotides with an amide internucleoside bond

  摘要：

  An improved method for the synthesis of 3-deoxy-3-carboxymethyl nucleosides was suggested. Oxidation of 5-O-benzoyl-1,2-O-isopropylidene-alpha-D-xylofuranose resulted in the 3-keto derivative, which was treated with triethylphosphonoacetate in the presence of sodium hydride to obtain the 3-deoxy-3-ethoxycarbonylmethylene derivative. Hydrogenation of the unsaturated compound proceeded strictly stereospecifically and gave the product with the ribo-configuration. Acetolysis of the resulting compound with AcOH-Ac2O-CH3SO3H led to 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-3-ethoxycarbonylmethyl-D-ribofuranose, whose interaction with persilylated nucleic bases gave 3-deoxy-3-ethoxycarbonylmethylnucleosides in a total yield of 42-49% from the starting compound.

  DOI：

  10.1134/s1068162009010099
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以91%的产率得到5-O-benzoyl-3-deoxy-3-ethoxycarbonylmethylene-1,2-O-isopropylidene-α-D-ribofuranose
  参考文献：
  名称：

  Synthesis of 3′-deoxy-3′-carboxymethylnucleosides, precursors of oligonucleotides with an amide internucleoside bond

  摘要：

  An improved method for the synthesis of 3-deoxy-3-carboxymethyl nucleosides was suggested. Oxidation of 5-O-benzoyl-1,2-O-isopropylidene-alpha-D-xylofuranose resulted in the 3-keto derivative, which was treated with triethylphosphonoacetate in the presence of sodium hydride to obtain the 3-deoxy-3-ethoxycarbonylmethylene derivative. Hydrogenation of the unsaturated compound proceeded strictly stereospecifically and gave the product with the ribo-configuration. Acetolysis of the resulting compound with AcOH-Ac2O-CH3SO3H led to 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-3-ethoxycarbonylmethyl-D-ribofuranose, whose interaction with persilylated nucleic bases gave 3-deoxy-3-ethoxycarbonylmethylnucleosides in a total yield of 42-49% from the starting compound.

  DOI：

  10.1134/s1068162009010099

文献信息

• Synthesis of 1-(5-amino-3,5-dideoxy-3-methoxycarbonylmethyl-β-d-ribofuranosyl)thymine
  作者：Dong-Mei Lu、Ji-Mei Min、Li-He Zhang

  DOI：10.1016/s0008-6215(99)00057-9

  日期：1999.4

  In order to synthesize amide-linked antisense oligonucleotides, a general chemical approach was developed for the synthesis of building blocks in which an amino group and a carboxylic group are contained at the 5' and 3' positions of a nucleoside. (C) 1999 Elsevier Science Ltd. All rights reserved.