(3S,4R)-4-benzyloxycarbonylamino-3-(triisopropylsilanyloxy)heptanoic acid | 325687-66-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,4R)-4-benzyloxycarbonylamino-3-(triisopropylsilanyloxy)heptanoic acid
• 英文别名: (3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-(triisopropyl-silanyloxy)hexanoic Acid；(3S,4R)-5-methyl-4-(phenylmethoxycarbonylamino)-3-tri(propan-2-yl)silyloxyhexanoic acid
• CAS: 325687-66-9
• 化学式: C₂₄H₄₁NO₅Si
• 分子量: 451.679
• InChiKey: CFDYVINFEGFPFL-JTHBVZDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R)-4-benzyloxycarbonylamino-3-(triisopropylsilanyloxy)heptanoic acid 在 palladium on activated charcoal 吗啉 、 吡啶 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 magnesium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl N-[(3S,6S,10S,11R,14S,15R,18S,21S)-18-[(4-methoxyphenyl)methyl]-15,19-dimethyl-3-(2-methylpropyl)-2,5,8,13,17,20-hexaoxo-6,11-di(propan-2-yl)-10-tri(propan-2-yl)silyloxy-7,16-dioxa-1,4,12,19-tetrazabicyclo[19.3.0]tetracosan-14-yl]carbamate
  参考文献：
  名称：

  Total synthesis of (−)-tamandarin B

  摘要：

  The synthesis of tamandarin B is described. Key steps in the synthesis of the macrocycle component include a diastereoselective ketone reduction, linear precursor formation via an activated pentafluorophenyl ester, and HATU-promoted cyclization. Side-chain coupling was achieved in excellent yield with the newly developed coupling reagent DEPBT. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01409-x
• 作为产物：
  描述：

  D-缬氨酸 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 钾硼氢 、 碳酸氢钠 、 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， 生成 (3S,4R)-4-benzyloxycarbonylamino-3-(triisopropylsilanyloxy)heptanoic acid
  参考文献：
  名称：

  Total Syntheses and Biological Investigations of Tamandarins A and B and Tamandarin A Analogs

  摘要：

  Tamandarins A (1) and B (2), two natural products similar in structure to didemnin B (3), were recently isolated from a Brazilian marine ascidian of the family Didemnidae. The cytotoxicity of 1 was reported to be somewhat more potent in vitro than that of 3 against various human cancer cell lines. The present account describes the first total syntheses of 1 and 2, and the syntheses of tamandarin A side chain analogues. The cytotoxicity data for these compounds show that the side chain modifications exhibit a parallel effect for both didemnins and tamandarins. This observation supports tamandarins' role as didemnins' mimic.

  DOI：

  10.1021/ja010222c

文献信息

• Tamandarin analogs and fragments thereof and methods of making and using
  申请人：Joullie M. Madeleine

  公开号：US20070149446A1

  公开（公告）日：2007-06-28

  The present invention is directed to a compound of Formula I wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , W, X, Y, and Z are defined herein. The compounds of the present invention are useful as anticancer agents. Specifically, the compounds are useful for treating or preventing cancer and tumor growth. The present invention is also directed to compositions comprising a compound according to the above formula. The present invention is also directed to methods of using a compound according to the above formula.

  本发明涉及公式I中R1、R2、R3、R4、R5、R6、W、X、Y和Z所定义的化合物。本发明的化合物可用作抗癌剂。具体而言，这些化合物可用于治疗或预防癌症和肿瘤生长。本发明还涉及包括上述公式中化合物的组合物。本发明还涉及使用上述公式中化合物的方法。
• Total synthesis of (−)-tamandarin B
  作者：Madeleine M Joullié、Padma Portonovo、Bo Liang、David J Richard

  DOI：10.1016/s0040-4039(00)01409-x

  日期：2000.12

  The synthesis of tamandarin B is described. Key steps in the synthesis of the macrocycle component include a diastereoselective ketone reduction, linear precursor formation via an activated pentafluorophenyl ester, and HATU-promoted cyclization. Side-chain coupling was achieved in excellent yield with the newly developed coupling reagent DEPBT. (C) 2000 Published by Elsevier Science Ltd.
• Total Syntheses and Biological Investigations of Tamandarins A and B and Tamandarin A Analogs
  作者：Bo Liang、David J. Richard、Padma S. Portonovo、Madeleine M. Joullié

  DOI：10.1021/ja010222c

  日期：2001.5.1

  Tamandarins A (1) and B (2), two natural products similar in structure to didemnin B (3), were recently isolated from a Brazilian marine ascidian of the family Didemnidae. The cytotoxicity of 1 was reported to be somewhat more potent in vitro than that of 3 against various human cancer cell lines. The present account describes the first total syntheses of 1 and 2, and the syntheses of tamandarin A side chain analogues. The cytotoxicity data for these compounds show that the side chain modifications exhibit a parallel effect for both didemnins and tamandarins. This observation supports tamandarins' role as didemnins' mimic.