(1R,2S,4R,5S)-1-<(benzyloxy)methyl>-2-(tert-butyloxy)-4-hydroxybicyclo<3.1.0>hexane | 169191-19-9

• 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: (1R,2S,4R,5S)-1-<(benzyloxy)methyl>-2-(tert-butyloxy)-4-hydroxybicyclo<3.1.0>hexane
• 英文别名: (1S,2S,4R,5S)-1-<(benzyloxy)methyl>-2-tert-butyloxy-4-hydroxybicyclo<3.1.0>hexane；(1S,2R,4S,5R)-5-((Benzyloxy)methyl)-4-(tert-butoxy)bicyclo[3.1.0]hexan-2-ol；(1S,2R,4S,5R)-4-[(2-methylpropan-2-yl)oxy]-5-(phenylmethoxymethyl)bicyclo[3.1.0]hexan-2-ol
• CAS: 169191-19-9
• 化学式: C₁₈H₂₆O₃
• 分子量: 290.403
• InChiKey: IJHNHTBGEIQMFA-CBZIJGRNSA-N

物化性质

• 沸点：
  384.1±22.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S,4R,5S)-1-<(benzyloxy)methyl>-2-(tert-butyloxy)-4-hydroxybicyclo<3.1.0>hexane 在 ammonium hydroxide 、 三氯化硼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 90.33h， 生成 (1R,2S,4S,5S)-1-hydroxymethyl-2-hydroxy-4-(6-amino-9-purinyl)bicyclo<3.1.0>hexane
  参考文献：
  名称：

  Synthesis, Conformational Analysis, and Biological Activity of a Rigid Carbocyclic Analogue of 2′-Deoxy Aristeromycin Built on a Bicyclo[3.1.0]hexane Template

  摘要：

  A new chiral synthesis of the pseudosugar synthon (1R,2S,4R,5S)-1-[(benzyloxy)methyl]-2-tert-butyloxy-4-hydroxybicyclo[3.1.0]hexane (12) is reported. This compound was used as a template for the construction of carbocyclic nucleoside 4, a conformationally rigid analogue of 2'-deoxyaristeromycin. The X-ray structure and H-1 NMR analysis confirmed the exclusive North [2'-exo ((2)E)] conformation of 4 which is vastly different from that of other non-rigid carbocyclic nucleosides. Compound 4 showed good in vitro antiviral activity against human cytomegalovirus and EBV with minimal cytotoxicity.

  DOI：

  10.1080/07328319608002382
• 作为产物：
  描述：

  (1S,4R,5S)-3-<(benzyloxy)methyl>-4-tert-butyloxy-5-hydroxy-2-cyclopenten-1-ol 在 三氢化钐 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 sodium hydride 、 mercury dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.58h， 生成 (1R,2S,4R,5S)-1-<(benzyloxy)methyl>-2-(tert-butyloxy)-4-hydroxybicyclo<3.1.0>hexane
  参考文献：
  名称：

  Synthesis, Conformational Analysis, and Biological Activity of a Rigid Carbocyclic Analogue of 2′-Deoxy Aristeromycin Built on a Bicyclo[3.1.0]hexane Template

  摘要：

  A new chiral synthesis of the pseudosugar synthon (1R,2S,4R,5S)-1-[(benzyloxy)methyl]-2-tert-butyloxy-4-hydroxybicyclo[3.1.0]hexane (12) is reported. This compound was used as a template for the construction of carbocyclic nucleoside 4, a conformationally rigid analogue of 2'-deoxyaristeromycin. The X-ray structure and H-1 NMR analysis confirmed the exclusive North [2'-exo ((2)E)] conformation of 4 which is vastly different from that of other non-rigid carbocyclic nucleosides. Compound 4 showed good in vitro antiviral activity against human cytomegalovirus and EBV with minimal cytotoxicity.

  DOI：

  10.1080/07328319608002382

文献信息

• Nucleosides with a Twist. Can Fixed Forms of Sugar Ring Pucker Influence Biological Activity in Nucleosides and Oligonucleotides?
  作者：Victor E. Marquez、Maqbool A. Siddiqui、Abdallah Ezzitouni、Pamela Russ、Jianying Wang、Richard W. Wagner、Mark D. Matteucci

  DOI：10.1021/jm960306+

  日期：1996.1.1

  of the pseudosugar rings into a Northern conformation, typical of A-DNA, was evident by the increase in Tm of the corresponding DNA/RNA heteroduplex. However, the rigid A-tract ODN caused loss of RNase H recruitment. A detailed conformational analysis of (N)-methanocarba-T (2) and (S)-methanocarba-T (12), as representative examples of conformationally rigid pseudorotational antipodes, revealed that

  已知溶液中核苷的糖部分以假旋转循环中定义的极端北部和南部构象之间的快速动态平衡存在。在当前的工作中，我们描述了双环[3.1.0]己烷模板如何将2'-脱氧-甲氨基甲酸酯-核苷1-5和12的环褶皱固定为与以下两个典型的极端构型之一相对应的值：核苷。固定的Northern构象1-5的合成是通过杂环基与手性碳环醇6 [[（1R，2S，4R，5S）-1-[（苄氧基）甲基] -2-（叔-丁氧基）-4-羟基ybicyclo [3.1.0]己烷]，而较早报道了南部构象异构体（S）-甲氨基甲酸酯-T（12）的合成。碳环胸苷（carba-T，13）作为参考，柔性碳环核苷。对这些化合物的抗病毒评价表明，它与北胸腺嘧啶核苷类似物2有关，具有很强的抗疱疹活性，它比参考标准阿昔洛韦对HSV-1和HSV-2的作用更强。（N）-Methanocarba-T（2）被进一步评估为短硫代脱氧核苷酸（ODN）硫代磷酸酯（5'-C