benzyl N,N'-bis(tert-butoxycarbonyl)-N-{N'-[2-(tert-butyldimethylsilyloxy)ethyl]-10-aminodecanoyloxyethyl}-10-aminodecanoate | 329309-22-0

• 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: benzyl N,N'-bis(tert-butoxycarbonyl)-N-{N'-[2-(tert-butyldimethylsilyloxy)ethyl]-10-aminodecanoyloxyethyl}-10-aminodecanoate
• 英文别名: 2-[(2-Methylpropan-2-yl)oxycarbonyl-(10-oxo-10-phenylmethoxydecyl)amino]ethyl 10-[2-[tert-butyl(dimethyl)silyl]oxyethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]decanoate
• CAS: 329309-22-0
• 化学式: C₄₇H₈₄N₂O₉Si
• 分子量: 849.277
• InChiKey: YHTGLGGXIZRDHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.01
• 重原子数：
  59
• 可旋转键数：
  36
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzyl N,N'-bis(tert-butoxycarbonyl)-N-{N'-[2-(tert-butyldimethylsilyloxy)ethyl]-10-aminodecanoyloxyethyl}-10-aminodecanoate 在 camphor-10-sulfonic acid 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以80%的产率得到benzyl N,N'-bis(tert-butoxycarbonyl)-N-[N'-(2-hydroxyethyl)-10-aminodecanoyloxyethyl]-10-aminodecanoate
  参考文献：
  名称：

  Synthesis and Ring Contraction Reactions of Polyazamacrolides

  摘要：

  The synthesis of three analogues of the single most abundant component of a ladybird beetle (Epilachna borealis) defensive secretion, the trimeric 42-membered polyazamacrolide PAML 681, is described. Construction of the nonnatural macrocyclic trimers began with the preparation of the corresponding monomeric segments, followed by their oligomerization and a final macrolactonization step of the activated linear trimeric hydroxy acid. The relative rates of the O-to-N acyl migrations that are characteristic of PAML 681 itself, as well as of the synthetic analogues, were investigated. These studies showed that changes in the substitution pattern adjacent to the nucleophilic nitrogen atom, along with changes in the size of the oxaazacyclic intermediates, have substantial effects on the polyazamacrolide rearrangement rates.

  DOI：

  10.1021/jo001247h
• 作为产物：
  描述：

  benzyl 10-hydroxydecanoate 在 4-二甲氨基吡啶 、 四丙基高钌酸铵 、 4 Angstroem MS 、 sodium cyanoborohydride 、 N-甲基吗啉氧化物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 65.5h， 生成 benzyl N,N'-bis(tert-butoxycarbonyl)-N-{N'-[2-(tert-butyldimethylsilyloxy)ethyl]-10-aminodecanoyloxyethyl}-10-aminodecanoate
  参考文献：
  名称：

  Synthesis and Ring Contraction Reactions of Polyazamacrolides

  摘要：

  The synthesis of three analogues of the single most abundant component of a ladybird beetle (Epilachna borealis) defensive secretion, the trimeric 42-membered polyazamacrolide PAML 681, is described. Construction of the nonnatural macrocyclic trimers began with the preparation of the corresponding monomeric segments, followed by their oligomerization and a final macrolactonization step of the activated linear trimeric hydroxy acid. The relative rates of the O-to-N acyl migrations that are characteristic of PAML 681 itself, as well as of the synthetic analogues, were investigated. These studies showed that changes in the substitution pattern adjacent to the nucleophilic nitrogen atom, along with changes in the size of the oxaazacyclic intermediates, have substantial effects on the polyazamacrolide rearrangement rates.

  DOI：

  10.1021/jo001247h

文献信息

• Synthesis and Ring Contraction Reactions of Polyazamacrolides
  作者：Silvina García-Rubio、Jerrold Meinwald

  DOI：10.1021/jo001247h

  日期：2001.2.1

  The synthesis of three analogues of the single most abundant component of a ladybird beetle (Epilachna borealis) defensive secretion, the trimeric 42-membered polyazamacrolide PAML 681, is described. Construction of the nonnatural macrocyclic trimers began with the preparation of the corresponding monomeric segments, followed by their oligomerization and a final macrolactonization step of the activated linear trimeric hydroxy acid. The relative rates of the O-to-N acyl migrations that are characteristic of PAML 681 itself, as well as of the synthetic analogues, were investigated. These studies showed that changes in the substitution pattern adjacent to the nucleophilic nitrogen atom, along with changes in the size of the oxaazacyclic intermediates, have substantial effects on the polyazamacrolide rearrangement rates.