N-benzyloxycarbonyl-HFB1 bis(acetonide) | 166039-13-0

• 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: N-benzyloxycarbonyl-HFB1 bis(acetonide)
• CAS: 166039-13-0
• 化学式: C₃₆H₆₁NO₇
• 分子量: 619.883
• InChiKey: HTWPTNJAAMMKMV-XOXZXSMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  44.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  95.48
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-HFB1 bis(acetonide) 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 (2S,4R)-8-[(4R,6S)-6-((S)-1-Amino-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-[(4S,5R)-2,2-dimethyl-5-((R)-1-methyl-pentyl)-[1,3]dioxolan-4-yl]-2-methyl-octan-4-ol
  参考文献：
  名称：

  Relative and Absolute Configuration of the Fumonisin B1 Backbone

  摘要：

  DOI：

  10.1021/ja00099a100
• 作为产物：
  描述：

  氯甲酸苄酯 在 邻苯二甲酸二甲酯 、 camphor-10-sulfonic acid 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 16.25h， 生成 N-benzyloxycarbonyl-HFB1 bis(acetonide)
  参考文献：
  名称：

  Chemical Transformation of Hydrolyzed Fumonisin B1 to Hydrolyzed Fumonisin B2

  摘要：

  The fumonisins, a series of sphingosine-analog mycotoxins produced by the ubiquitous corn contaminant Fusarium moniliforme, are an important food safety concern because they are tumor promoters with sufficient chemical stability to persist through normal food processing. Removing propane-1,2,3-tricarboxylic acid side chains produces hydrolyzed fumonisins (HF), including HFB1 and HFB2, which retain biological activity. Detection of hydrolyzed fumonisins in food products has created a need for efficient methods to prepare them for use as analytical standards. In the present study conversion of the more abundant HFB1 to HFB2 was accomplished by selectively protecting the hydroxyl groups to be retained as the bis(acetonide), deoxygenating the remaining free hydroxyl, and removing the blocking groups. Deoxygenation was accomplished by two methods: (i) free radical-initiated homolytic cleavage of the O-phenoxythiocarbonyl ester in the presence of tributyltin hydride and (ii) LiAlH4 reduction of the tosylate ester.

  DOI：

  10.1021/jf00056a006