methyl 3-(tert-butyldiphenylsilanyloxy)-2-(4-methoxybenzyloxy)propionate | 326606-28-4

• 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: methyl 3-(tert-butyldiphenylsilanyloxy)-2-(4-methoxybenzyloxy)propionate
• 英文别名: methyl (2R)-3-[tert-butyl(diphenyl)silyl]oxy-2-[(4-methoxyphenyl)methoxy]propanoate
• CAS: 326606-28-4
• 化学式: C₂₈H₃₄O₅Si
• 分子量: 478.66
• InChiKey: FEWVFAXUFJLMOI-AREMUKBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(tert-butyldiphenylsilanyloxy)-2-(4-methoxybenzyloxy)propionate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-(tert-butyldiphenylsilanyloxy)-2-(4-methoxybenzyloxy)-5-methylhex-5-en-3-ol
  参考文献：
  名称：

  Stereochemical Assignment of the C₁−C₆ Fragment of Psymberin by Synthesis and Natural Product Degradation

  摘要：

  Psymberin is a sponge-derived natural product that shows striking selectivity as a cytotoxic agent. Conformational mobility has precluded stereochemical assignment for the acyl fragment of this molecule (psymberic acid) by NMR. Herein we report stereoselective syntheses of all four stereoisomers of psymberic acid. A comparison of the acid-mediated cyclization products of these compounds to the product of psymberin's acidic methanolysis showed the stereochemical configuration of this fragment to be 4S, 5S.

  DOI：

  10.1021/ol051396s
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 咪唑 、 三氟化硼四氢呋喃络合物 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 1.0h， 生成 methyl 3-(tert-butyldiphenylsilanyloxy)-2-(4-methoxybenzyloxy)propionate
  参考文献：
  名称：

  Stereochemical Assignment of the C₁−C₆ Fragment of Psymberin by Synthesis and Natural Product Degradation

  摘要：

  Psymberin is a sponge-derived natural product that shows striking selectivity as a cytotoxic agent. Conformational mobility has precluded stereochemical assignment for the acyl fragment of this molecule (psymberic acid) by NMR. Herein we report stereoselective syntheses of all four stereoisomers of psymberic acid. A comparison of the acid-mediated cyclization products of these compounds to the product of psymberin's acidic methanolysis showed the stereochemical configuration of this fragment to be 4S, 5S.

  DOI：

  10.1021/ol051396s

文献信息

• Synthesis of the Left-Hand Portion of Geldanamycin Using an Anti Glycolate Aldol Reaction
  作者：Merritt B. Andrus、Erik L. Meredith、B. B. V. Soma Sekhar

  DOI：10.1021/ol0068997

  日期：2001.1.1

  [figure: see text] A synthesis of the left-hand portion of the ansamycin antitumor natural product geldanamycin is reported. An advanced intermediate incorporates the methoxyquinone precursor as a pentasubstituted benzene with a 10-carbon chain that contains 4 of the 6 stereocenters. The key reaction is a novel anti glycolate aldol reaction with a new diaryl-4-oxapyrone used to generate the C-11, C-12

  [图：见正文]据报道，安沙霉素抗肿瘤天然产物格尔德霉素的左侧部分已合成。高级中间体将甲氧基醌前体作为具有10个碳链的五取代苯包含6个立体中心中的4个。关键反应是与新型二芳基-4-氧杂蒽酮发生的新型抗羟乙酸羟醛反应，该新二芳基-4-氧杂吡酮用于生成C-11，C-12羟基，甲氧基官能团。
• Stereochemical Assignment of the C₁−C₆ Fragment of Psymberin by Synthesis and Natural Product Degradation
  作者：Michael E. Green、Jason C. Rech、Paul E. Floreancig

  DOI：10.1021/ol051396s

  日期：2005.9.1

  Psymberin is a sponge-derived natural product that shows striking selectivity as a cytotoxic agent. Conformational mobility has precluded stereochemical assignment for the acyl fragment of this molecule (psymberic acid) by NMR. Herein we report stereoselective syntheses of all four stereoisomers of psymberic acid. A comparison of the acid-mediated cyclization products of these compounds to the product of psymberin's acidic methanolysis showed the stereochemical configuration of this fragment to be 4S, 5S.