[(3aR,4R,6aS)-2,2-dioxo-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3,2]dioxathiol-4-yl]methoxy-tert-butyl-diphenylsilane | 367270-92-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: [(3aR,4R,6aS)-2,2-dioxo-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3,2]dioxathiol-4-yl]methoxy-tert-butyl-diphenylsilane
• CAS: 367270-92-6
• 化学式: C₂₁H₂₆O₆SSi
• 分子量: 434.585
• InChiKey: GIVSVAIAULGPIK-HSALFYBXSA-N

物化性质

• 沸点：
  509.4±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3aR,4R,6aS)-2,2-dioxo-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3,2]dioxathiol-4-yl]methoxy-tert-butyl-diphenylsilane 在 硫酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 3.5h， 生成 5'-O-(t-butyldiphenylsilyl)-1'-deoxy-2'-isoadenosine
  参考文献：
  名称：

  Synthetic Approaches to Nuclease-Resistant, Nonnatural Dinucleotides of Anti-Hiv Integrase Interest

  摘要：

  New, nonnatural dinucleotide 5'-monophosphates with a surrogate isonucleoside component of L-related stereochemistry, have been synthesized. Structures of the target compounds were confirmed by multinuclear NMR spectra (H-1, C-13, P-31, COSY), UV hypochromicity, FAB HRMS data and X-ray crystallography. These compounds are totally resistant to cleavage by 3'- and 5'-exonucleases. Dinucleotides of this study with a terminal L-isonucleoside component showed remarkable selectivity for inhibition of the strand transfer step of HIV-1 integrase. To the best of our knowledge, these compounds represent only the second example of this type of selectivity of inhibition of the strand transfer step.

  DOI：

  10.1080/15257770500265703
• 作为产物：
  描述：

  2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3R,4S)-disulfite 在 ruthenium trichloride 、 sodium periodate 作用下， 以 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

文献信息

• A New Approach for the Synthesis of Novel 5‐Substituted Isodeoxyuridine Analogs
  作者：Sven Guenther、Vasu Nair

  DOI：10.1081/ncn-120027827

  日期：2004.1.1

  synthons for the preparation of isodeoxyuridines through direct nucleophilic substitution reactions. These substitution reactions have exceptional regioselectivity. The products of the reactions served as key precursors for the synthesis of 5‐substituted isodeoxyuridines via the Stille and Heck coupling reactions. Interestingly, unprotected nucleosides could be used in these metal‐mediated functionalizations

  碳水化合物的环状硫酸盐为通过直接亲核取代反应制备异脱氧尿苷提供了极好的合成子。这些取代反应具有特殊的区域选择性。这些反应的产物是通过 Stille 和 Heck 偶联反应合成 5-取代异脱氧尿苷的关键前体。有趣的是，未受保护的核苷可用于这些金属介导的功能化。这些方法是通用的，可以很容易地获得各种 C-5 功能化的异构脱氧尿苷，但也有可能扩展到其他核苷类似物。†为了纪念和庆祝 Leroy B. Townsend 教授 70 岁生日。
• Synthetic Approaches to Nuclease-Resistant, Nonnatural Dinucleotides of Anti-Hiv Integrase Interest
  作者：Guochen Chi、Vasu Nair

  DOI：10.1080/15257770500265703

  日期：2005.9.1

  New, nonnatural dinucleotide 5'-monophosphates with a surrogate isonucleoside component of L-related stereochemistry, have been synthesized. Structures of the target compounds were confirmed by multinuclear NMR spectra (H-1, C-13, P-31, COSY), UV hypochromicity, FAB HRMS data and X-ray crystallography. These compounds are totally resistant to cleavage by 3'- and 5'-exonucleases. Dinucleotides of this study with a terminal L-isonucleoside component showed remarkable selectivity for inhibition of the strand transfer step of HIV-1 integrase. To the best of our knowledge, these compounds represent only the second example of this type of selectivity of inhibition of the strand transfer step.
• 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。