(3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester | 325687-69-2

• 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-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester
• 英文别名: [(2S)-3-methyl-1-oxo-1-(2,3,4,5,6-pentafluorophenoxy)butan-2-yl] (3S,4R)-5-methyl-4-(phenylmethoxycarbonylamino)-3-tri(propan-2-yl)silyloxyhexanoate
• CAS: 325687-69-2
• 化学式: C₃₅H₄₈F₅NO₇Si
• 分子量: 717.846
• InChiKey: DNOHQWKFGHYJGG-MAPBSZMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.76
• 重原子数：
  49
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 氢气 、 N,N-二异丙基乙胺 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 、 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 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 tamandarin B
  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
• 作为产物：
  描述：

  L-缬氨酸 在 四丁基碘化铵 吗啉 、 吡啶 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 硫酸 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester
  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

• Total Synthesis and Biological Evaluation of Tamandarin B Analogues
  作者：Javier Adrio、Carmen Cuevas、Ignacio Manzanares、Madeleine M. Joullié

  DOI：10.1021/jo070412r

  日期：2007.7.1

  Tamandarins A and B are a class of marine natural cyclodepsipeptides with structures and biological activities closely related to those of the didemnins. The easier synthetic access to tamandarins accelerates the preparation of new macrocyclic derivatives of this family of antitumor, antiviral, and immunosuppressive compounds. The optimization of the previously reported synthetic route to tamandarins

  丹丹素A和B是一类海洋天然环二肽，其结构和生物活性与二羟肌酐密切相关。合成的坦丹更容易获得，从而加快了该抗肿瘤，抗病毒和免疫抑制化合物家族新的大环衍生物的制备。通过将大内酰胺化位点从Nst 1和Thr 6更改为Pro 4和N，O -Me 2 Tyr 5来优化先前报道的合成坦丹林的合成路线残留物导致反应产率的显着提高。使用这种新的合成方法，制备了tamandarin B的四个新的大环类似物，并评估了其抗癌活性。这些结果提供了进一步的见解，其坦丹林和双精胺的结构活性关系。
• 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.
• Synthesis and Biological Evaluation of Tamandarin B Analogues
  作者：Javier Adrio、Carmen Cuevas、Ignacio Manzanares、Madeleine M. Joullié

  DOI：10.1021/ol0530023

  日期：2006.2.1

  [GRAPHICS]The synthesis of two tamandarin B analogues in which the N,O-Me(2)Tyr(5) unit was replaced by N-Me-phenylaianine (N-MePhe(5)) and (S)-2(methylamino)-3-(naphthalen-2-yl)propanoic acid (N-MeNaphth(5)) is described. The choice of the macrocyclization site was crucial to achieve satisfactory macrolactamization. Coupling between norstatine (Nst(1)) and threonine (Thr(6)) afforded only a 15% yield, while lactamization between proline (Pro(4)) and the aromatic moiety could be achieved in 65% yield.