2,3,5-tri-O-tert-butyldimethylsilyl-α-D-arabinofuranosyl bromide | 1025026-60-1

• 分子结构分类: 有机化合物
• 英文名称: 2,3,5-tri-O-tert-butyldimethylsilyl-α-D-arabinofuranosyl bromide
• CAS: 1025026-60-1
• 化学式: C₂₃H₅₁BrO₄Si₃
• 分子量: 555.816
• InChiKey: SLGAAIFAGZIEEC-ZRNYENFQSA-N

物化性质

• 沸点：
  452.4±45.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.91
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-tert-butyldimethylsilyl-α-D-arabinofuranosyl bromide 在 palladium on activated charcoal ammonium hydroxide 、 氟化铵 、 氢气 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 25.0h， 生成 [(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl] [(2Z)-3,7-dimethylocta-2,6-dienyl] hydrogen phosphate
  参考文献：
  名称：

  Stereoselective synthesis of farnesylphosphoryl β-d-arabinofuranose

  摘要：

  Decaprenylphosphoryl beta-D-arabinofuranose (DPA) is a key arabinose donor in mycobacteria. In an effort to establish a practical synthetic scheme for DPA, the synthesis of nerylphosphoryl and farnesylphosphoryl beta-D-arabinofuranoses has been developed. The products were obtained by coupling of a suitably protected P-D-arabinofuranosyl phosphate intermediate with activated forms of the C-10 nerol and C-15 trans,trans-farnesol and subsequent deprotection. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.151
• 作为产物：
  描述：

  (3S,4R,5R)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-ol 在 吡啶 、 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 生成 2,3,5-tri-O-tert-butyldimethylsilyl-α-D-arabinofuranosyl bromide
  参考文献：
  名称：

  Stereoselective synthesis of farnesylphosphoryl β-d-arabinofuranose

  摘要：

  Decaprenylphosphoryl beta-D-arabinofuranose (DPA) is a key arabinose donor in mycobacteria. In an effort to establish a practical synthetic scheme for DPA, the synthesis of nerylphosphoryl and farnesylphosphoryl beta-D-arabinofuranoses has been developed. The products were obtained by coupling of a suitably protected P-D-arabinofuranosyl phosphate intermediate with activated forms of the C-10 nerol and C-15 trans,trans-farnesol and subsequent deprotection. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.151

文献信息

• <i>N</i>‐Glycosyl‐<i>N</i>′‐[<i>p</i>‐(isoamyloxy)phenyl]‐thiourea Derivatives: Potential Anti‐TB Therapeutic Agents
  作者：Avraham Liav、Shiva K. Angala、Patrick J. Brennan

  DOI：10.1080/00397910701865777

  日期：2008.3.28

  Abstract Thiocarlide (THC; N,N′‐bis[p‐(isoamyloxy)phenyl]‐thiourea; also known as Isoxyl®) has been used in the past as an anti‐tuberculosis agent. In an effort to improve the therapeutic value of THC, several N‐glycosyl‐N′‐[p‐(isoamyloxy)phenyl]‐thiourea derivatives were synthesized by coupling an aniline derivative and glycosyl isothiocyanates. The minimum inhibitory concentration (MIC) values of

  摘要 Thiocarlide (THC; N,N'-bis[p-(isoamyloxy)phenyl]-thiourea; 也称为 Isoxyl®) 过去曾被用作抗结核剂。为了提高 THC 的治疗价值，通过将苯胺衍生物和糖基异硫氰酸酯偶联，合成了几种 N-糖基-N'-[对（异戊氧基）苯基]-硫脲衍生物。确定了新产品对结核分枝杆菌的最低抑菌浓度（MIC）值。