2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3S,4S)-diol | 215031-98-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3S,4S)-diol
• 英文别名: (2R,3S,4S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolane-3,4-diol
• CAS: 215031-98-4
• 化学式: C₂₁H₂₈O₄Si
• 分子量: 372.536
• InChiKey: BDWXJQOUUVTPDU-ZCNNSNEGSA-N

物化性质

• 沸点：
  470.4±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3S,4S)-diol 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 作用下， 以 吡啶 、 四氯化碳 、 水 、 乙腈 为溶剂， 生成 [(3aR,4R,6aS)-2,2-dioxo-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3,2]dioxathiol-4-yl]methoxy-tert-butyl-diphenylsilane
  参考文献：
  名称：

  异构核苷的新通用合成

  摘要：

  描述了一种有效的合成异核苷的新方法。合成中的关键步骤是嘌呤和嘧啶碱基与碳水化合物中间体的环状硫酸盐直接偶联。该反应以高区域专一性和立体专一性进行。

  DOI：

  10.1016/s0040-4039(01)01118-2
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 、 1,4-anhydro-D-ribitol 在 吡啶 作用下， 生成 2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3S,4S)-diol
  参考文献：
  名称：

  Synthesis and Antiviral Studies of Unsaturated Analogues of Isomeric Dideoxynucleosides

  摘要：

  Novel isomeric dideoxynucleosides with unsaturation in the carbohydrate moiety have been synthesized. For example, isod4A was synthesized through a rearrangement reaction involving a cyclonucleoside. Support for the structures of both purine and pyrimidine d4 compounds came from UV, NMR, HRMS and single crystal Xray data. Interestingly, the single crystal X-ray data for isod4C shows that the base is almost orthogonal to the carbon-carbon double bond of the sugar moiety. Consistent with this is the observation that the UV data of this compound does not show a bathochromic shift compared to the saturated compound implying that the pi-bond is not in conjugation with the pyrimidine base.

  DOI：

  10.1080/07328319908044614

文献信息

• Synthesis and Antiviral Studies of Unsaturated Analogues of Isomeric Dideoxynucleosides
  作者：Sanjib Bera、Travis Mickle、Vasu Nair

  DOI：10.1080/07328319908044614

  日期：1999.11

  Novel isomeric dideoxynucleosides with unsaturation in the carbohydrate moiety have been synthesized. For example, isod4A was synthesized through a rearrangement reaction involving a cyclonucleoside. Support for the structures of both purine and pyrimidine d4 compounds came from UV, NMR, HRMS and single crystal Xray data. Interestingly, the single crystal X-ray data for isod4C shows that the base is almost orthogonal to the carbon-carbon double bond of the sugar moiety. Consistent with this is the observation that the UV data of this compound does not show a bathochromic shift compared to the saturated compound implying that the pi-bond is not in conjugation with the pyrimidine base.
• A new general synthesis of isomeric nucleosides
  作者：Sanjib Bera、Vasu Nair

  DOI：10.1016/s0040-4039(01)01118-2

  日期：2001.8

  An efficient new method for the synthesis of isonucleosides is described. The key step in the synthesis was the direct coupling of purine and pyrimidine bases with the cyclic sulfate of a carbohydrate intermediate. This reaction proceeded with high regiospecificity and stereospecificity.

  描述了一种有效的合成异核苷的新方法。合成中的关键步骤是嘌呤和嘧啶碱基与碳水化合物中间体的环状硫酸盐直接偶联。该反应以高区域专一性和立体专一性进行。