(3S,4R)-4-(tert-butoxycarbonylamino)-3-hydroxy-5-methylhexanoic acid methyl ester | 663918-98-7

• 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-(tert-butoxycarbonylamino)-3-hydroxy-5-methylhexanoic acid methyl ester
• 英文别名: 4R-tert-butoxycarbonylamino-3S-hydroxy-5-methylhexanoic acid methyl ester；(3S,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-5-methylhexanoic Acid Methyl Ester；methyl (3S,4R)-3-hydroxy-5-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 663918-98-7
• 化学式: C₁₃H₂₅NO₅
• 分子量: 275.345
• InChiKey: BXCPYVYTJUUMQM-GXSJLCMTSA-N

物化性质

• 沸点：
  395.6±32.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 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-(tert-butoxycarbonylamino)-3-hydroxy-5-methylhexanoic acid methyl ester 在 4-二甲氨基吡啶 、 lithium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 4R-tert-butoxycarbonylamino-3S-hydroxy-5-methylhexanoic acid 2,2,2-trichloroethyl ester
  参考文献：
  名称：

  Total Synthesis of Spiruchostatin A, a Potent Histone Deacetylase Inhibitor

  摘要：

  The total synthesis of spiruchostatin A was accomplished, unambiguously confirming its structure. Key steps included the use of the Nagao thiazolidinethione auxiliary for a diastereoselective acetate aldol reaction and as an activated acylating agent for amide formation, and macrolactonization by the Yamaguchi protocol. Spiruchostatin A is shown to have biological activity similar to that of FK228, a potent histone deacetylase (HDAC) inhibitor in clinical trials. The spiruchostatin A analogue, epimeric at the beta-hydroxy acid, is inactive, highlighting the importance of stereochemistry at this position for interactions with HDACs.

  DOI：

  10.1021/ja039258q
• 作为产物：
  描述：

  D-缬氨酸 在 吡啶 、 钾硼氢 、 碳酸氢钠 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.58h， 生成 (3S,4R)-4-(tert-butoxycarbonylamino)-3-hydroxy-5-methylhexanoic acid methyl ester
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Tamandarin B Analogues

  摘要：

  [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.

  DOI：

  10.1021/ol0530023

文献信息

• Total Synthesis and Stereochemical Revision of Burkholdac A
  作者：Zhengshuang Xu、Tao Ye、Junyang Liu、Xiao Ma、Yuqing Liu、Zhuo Wang、Shuqin Kwong、Qi Ren、Shoubin Tang、Yi Meng

  DOI：10.1055/s-0031-1290339

  日期：2012.3

  A stereocontrolled total synthesis of burkholdac A was completed, leading to a revision of the reported stereochemistry. burkholdac A - total synthesis - antitumor - stereochemical assignment

  立体控制的Burkholdac A的总合成完成，从而导致了报道的立体化学的修订。 burkholdac A-全合成-抗肿瘤-立体化学分配
• 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。
• 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。
• An efficient synthesis of the tamandarin B macrocycle
  作者：Kenneth M. Lassen、Jisun Lee、Madeleine M. Joullié

  DOI：10.1016/j.tetlet.2009.12.091

  日期：2010.3

  A reliable, high yielding cyclization protocol for the macrocycle of tamandarin B is presented. This strategy will facilitate the synthesis of side chain analogs. (C) 2009 Elsevier Ltd. All rights reserved.
• US8030279B2
  申请人：——

  公开号：US8030279B2

  公开（公告）日：2011-10-04