1,5-anhydro-4-O-p-methoxybenzyl-D-ribo-hex-1-enitol | 1512853-01-8

• 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: 1,5-anhydro-4-O-p-methoxybenzyl-D-ribo-hex-1-enitol
• 英文别名: (2R,3S,4S)-3-[(4-methoxyphenyl)methoxy]-2-methyl-3,4-dihydro-2H-pyran-4-ol
• CAS: 1512853-01-8
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: NSNJFXHCRQFOEK-DDTOSNHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-4-O-p-methoxybenzyl-D-ribo-hex-1-enitol 在 咪唑 、 [ReOCl3(OPPh3)(SMe2)] 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 4.0h， 生成 phenyl 3-O-tert-butyldimethylsilyl-2,6-dideoxy-4-O-p-methoxybenzyl-1-thio-β-D-ribohexapyranoside
  参考文献：
  名称：

  Catalytic Stereoselective Synthesis of β-Digitoxosides: Direct Synthesis of Digitoxin and C1′-epi-Digitoxin

  摘要：

  A mild and atom-economic rhenium(V)-catalyzed stereoselective synthesis of beta-D-digitoxosides from 6-deoxy-D-allals has been described. This beta-selective glycosylation was achieved probably because of the formation of corresponding alpha-digitoxosides disfavored by 1,3-diaxial interaction. In addition, this method has been successfully applied to the synthesis of digitoxin trisaccharide glycal for the direct synthesis of digitwdn and C1'-epi-digitoxin.

  DOI：

  10.1021/jo4021419
• 作为产物：
  描述：

  1,5-anhydro-3-O-benzyl-D-ribo-hex-1-enitol 在 LiDBB 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1,5-anhydro-4-O-p-methoxybenzyl-D-ribo-hex-1-enitol
  参考文献：
  名称：

  Catalytic Stereoselective Synthesis of β-Digitoxosides: Direct Synthesis of Digitoxin and C1′-epi-Digitoxin

  摘要：

  A mild and atom-economic rhenium(V)-catalyzed stereoselective synthesis of beta-D-digitoxosides from 6-deoxy-D-allals has been described. This beta-selective glycosylation was achieved probably because of the formation of corresponding alpha-digitoxosides disfavored by 1,3-diaxial interaction. In addition, this method has been successfully applied to the synthesis of digitoxin trisaccharide glycal for the direct synthesis of digitwdn and C1'-epi-digitoxin.

  DOI：

  10.1021/jo4021419

文献信息

• Selective deprotection of benzyl (Bn) ethers in the presence of para-methoxybenzyl (PMB) ethers
  作者：Xiaohua Li、Zachary Saleh、Brian Egri、Ali Hourani、Luke Harding、Kedar N. Baryal、Jianglong Zhu

  DOI：10.1016/j.tetlet.2015.01.105

  日期：2015.3

  Substituted benzyl ethers have been widely used as readily manipulatable protecting groups for organic synthesis. It is known that electron-rich para-methoxybenzyl (PMB) ethers can be selectively deprotected over benzyl or other electron-poor benzyl ethers under oxidative conditions. In this presentation, we will describe an approach for selective deprotection of benzyl ethers in the presence of PMB

  取代的苄基醚已被广泛用作有机合成中易于操作的保护基。已知在氧化条件下，富电子的对-甲氧基苄基（PMB）醚可以在苄基或其他贫电子的苄基醚上选择性地脱保护。在此介绍中，我们将描述一种在还原条件下在PMB醚存在下对苄基醚进行选择性脱保护的方法。这种新方法应补充在有机合成中，尤其是在碳水化合物合成中利用取代的苄基醚的现有策略。