3,5-di-O-benzyl-1,2-di-O-isopropylidene-3-C-(methanesulfonyloxymethyl)-α-D-ribofuranose | 858128-95-7

• 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: 3,5-di-O-benzyl-1,2-di-O-isopropylidene-3-C-(methanesulfonyloxymethyl)-α-D-ribofuranose
• 英文别名: 3-C-(methanesulfonyloxymethyl)-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose；[(3aR,5R,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-5-(phenylmethoxymethyl)-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-yl]methyl methanesulfonate
• CAS: 858128-95-7
• 化学式: C₂₄H₃₀O₈S
• 分子量: 478.563
• InChiKey: PGJBQSVDWSWVAB-JTOYRKQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,5-di-O-benzyl-1,2-di-O-isopropylidene-3-C-(methanesulfonyloxymethyl)-α-D-ribofuranose 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以58%的产率得到3-C-fluoromethyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose
  参考文献：
  名称：

  Synthesis and anti-hepatitis C virus (HCV) activity of 3′-C-substituted-methyl pyrimidine and purine nucleosides

  摘要：

  On the basis of potent anti-hepatitis C virus (HCV) activity of 2'-C-hydroxymethyladenosine, 3'-C-substituted-methyl-ribofuranosyl pyrimidine and purine nucleosides were designed and synthesized from D-xylose. Among compounds tested, all adenine analogues, 4a, 4d, and 4g showed significant anti-HCV activity in a replicon-based cell assay irrespective of the substituent (Y = OH, N-3, or F) at the 3'-C-substituted methyl position, among which 4g (Y = N3) was the most potent, but it is also cytotoxic. This study guarantees the 3'-C-substituted-methyl nucleoside serves as a new template for the development of new anti-HCV agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.002
• 作为产物：
  描述：

  3,5-di-O-benzyl-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose 在 吡啶 作用下， 生成 3,5-di-O-benzyl-1,2-di-O-isopropylidene-3-C-(methanesulfonyloxymethyl)-α-D-ribofuranose
  参考文献：
  名称：

  E型构象的α-d构型双环核苷：合成和平行RNA识别。

  摘要：

  合成了被2'-3'-稠合的氧杂环丁烷环严格限制在E-型构象中的α- d-阿拉伯糖基构型的双环核苷。朝向目标化合物的几种合成策略被描述，并且从成功制备d -木糖衍生物是基于双键的钌-介导的裂解，一个S Ñ 2反转在2-位，得到阿糖-构型，核碱基偶联，最后闭环得到氧杂环丁烷环。该Ë-型构象通过分子建模和NMR确认。核苷被掺入短的α-DNA序列中。在混合的嘧啶环境中，它们识别亲和力主要增加的互补平行RNA序列和亲和力降低的互补平行DNA序列。本双环类似物代表第一个构象受限的α-DNA类似物，以改善与α-DNA单体的混合器中的核酸识别。

  DOI：

  10.1021/jo0500380

文献信息

• An α-<scp>d</scp>-Configured Bicyclic Nucleoside Restricted in an <i>E</i>-type Conformation:  Synthesis and Parallel RNA Recognition
  作者：Pawan K. Sharma、Michael Petersen、Poul Nielsen

  DOI：10.1021/jo0500380

  日期：2005.6.1

  oxetane ring. The E-type conformation is confirmed by molecular modeling and NMR. The nucleoside is incorporated into short α-DNA sequences. In a mixed pyrimidine context, these recognize complementary parallel RNA-sequences with mainly increased affinity and complementary parallel DNA-sequences with decreased affinity. The present bicyclic analogue represents the first conformationally restricted α-DNA-analogue

  合成了被2'-3'-稠合的氧杂环丁烷环严格限制在E-型构象中的α- d-阿拉伯糖基构型的双环核苷。朝向目标化合物的几种合成策略被描述，并且从成功制备d -木糖衍生物是基于双键的钌-介导的裂解，一个S Ñ 2反转在2-位，得到阿糖-构型，核碱基偶联，最后闭环得到氧杂环丁烷环。该Ë-型构象通过分子建模和NMR确认。核苷被掺入短的α-DNA序列中。在混合的嘧啶环境中，它们识别亲和力主要增加的互补平行RNA序列和亲和力降低的互补平行DNA序列。本双环类似物代表第一个构象受限的α-DNA类似物，以改善与α-DNA单体的混合器中的核酸识别。
• Synthesis and anti-hepatitis C virus (HCV) activity of 3′-C-substituted-methyl pyrimidine and purine nucleosides
  作者：Won Jun Choi、Yu Min Kim、Hea Ok Kim、Hyuk Woo Lee、Dong-Eun Kim、Kwang-su Park、Youhoon Chong、Lak Shin Jeong

  DOI：10.1016/j.bmc.2010.05.002

  日期：2010.7

  On the basis of potent anti-hepatitis C virus (HCV) activity of 2'-C-hydroxymethyladenosine, 3'-C-substituted-methyl-ribofuranosyl pyrimidine and purine nucleosides were designed and synthesized from D-xylose. Among compounds tested, all adenine analogues, 4a, 4d, and 4g showed significant anti-HCV activity in a replicon-based cell assay irrespective of the substituent (Y = OH, N-3, or F) at the 3'-C-substituted methyl position, among which 4g (Y = N3) was the most potent, but it is also cytotoxic. This study guarantees the 3'-C-substituted-methyl nucleoside serves as a new template for the development of new anti-HCV agents. (C) 2010 Elsevier Ltd. All rights reserved.