N-benzyloxycarbonyl-HFB1 | 166039-12-9

• 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: N-benzyloxycarbonyl-HFB1
• 英文别名: benzyl N-[(2S,3S,5R,10R,12S,14S,15R,16R)-3,5,10,14,15-pentahydroxy-12,16-dimethylicosan-2-yl]carbamate
• CAS: 166039-12-9
• 化学式: C₃₀H₅₃NO₇
• 分子量: 539.753
• InChiKey: JRFKBMJTIVTJPY-YKNOUCEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  38
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-HFB1 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 邻苯二甲酸二甲酯 、 camphor-10-sulfonic acid 、 氢气 作用下， 25.0 ℃ 、310.27 kPa 条件下， 反应 16.0h， 生成 Toluene-4-sulfonic acid (R)-5-[(4R,6S)-6-((S)-1-amino-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-{(R)-3-[(4S,5R)-2,2-dimethyl-5-((R)-1-methyl-pentyl)-[1,3]dioxolan-4-yl]-2-methyl-propyl}-pentyl ester
  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
• 作为产物：
  描述：

  fumonisin B1 在 氢氧化钾 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 24.0h， 生成 N-benzyloxycarbonyl-HFB1
  参考文献：
  名称：

  Relative and Absolute Configuration of the Fumonisin B1 Backbone

  摘要：

  DOI：

  10.1021/ja00099a100

文献信息

• Chemical Transformation of Hydrolyzed Fumonisin B1 to Hydrolyzed Fumonisin B2
  作者：Farid A. Badria、Hamed K. Abbas、W. Thomas Shier

  DOI：10.1021/jf00056a006

  日期：1995.8

  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.
• Relative and Absolute Configuration of the Fumonisin B1 Backbone
  作者：Thomas R. Hoye、Jorge I. Jimenez、W. Thomas Shier

  DOI：10.1021/ja00099a100

  日期：1994.10