β-alanine 2-(trimethylsilyl)ethyl ester | 162472-68-6

• 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: β-alanine 2-(trimethylsilyl)ethyl ester
• 英文别名: 2-Trimethylsilylethyl 3-aminopropanoate
• CAS: 162472-68-6
• 化学式: C₈H₁₉NO₂Si
• 分子量: 189.33
• InChiKey: DMDJJSJVIBBDQG-UHFFFAOYSA-N

物化性质

• 沸点：
  234.6±20.0 °C(Predicted)
• 密度：
  0.930±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  β-alanine 2-(trimethylsilyl)ethyl ester 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium hydroxide 、 甲酸 、 WCSI*HCl 、 氢气 、 sodium hydride 、 三乙胺 、 焦碳酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[(R)-2-[(E)-4-((2S,3S,4R,5S)-4-Acetoxy-3-methyl-5-phenyl-tetrahydro-furan-2-yl)-but-2-enoylamino]-3-(4-methoxy-phenyl)-propionylamino]-propionic acid 2-trimethylsilanyl-ethyl ester
  参考文献：
  名称：

  The Absolute Stereostructure of Arenastatin A, a Potent Cytotoxic Depsipeptide from the Okinawan Marine Sponge Dysidea arenaria.

  摘要：

  根据核磁共振和合成研究，确定了从冲绳海洋海绵 Dysidea arenaria 中分离出来的阿那曲汀 A (1) 的绝对立体结构。阿仑他汀 A (1) 是一种环状去肽类化合物，对 KB 细胞具有极强的细胞毒性，IC50 为 5pg/ml 。

  DOI：

  10.1248/cpb.42.2196
• 作为产物：
  描述：

  在 palladium on activated charcoal 甲酸 、 氢气 作用下， 以 甲醇 为溶剂， 生成 β-alanine 2-(trimethylsilyl)ethyl ester
  参考文献：
  名称：

  A Total Synthesis of Arenastatin A, an Extremely Potent Cytotoxic Depsipeptide, from the Okinawan Marine Sponge Dysidea arenaria.

  摘要：

  一种不对称合成环状脱肽类化合物arenastatin A (1)的研究已完成，该化合物是从海绵Dysidea arenaria中分离得到的，并对KB细胞表现出极强的细胞毒性，其IC50为5 pg/ml。

  DOI：

  10.1248/cpb.42.2394

文献信息

• Preparation of potential inhibitors of the mur-Pathway enzymes on solid support using an acetal linker
  作者：Milana Maletic、Jelena Antonic、Aaron Leeman、Gina Santorelli、Sherman Waddell

  DOI：10.1016/s0960-894x(03)00043-x

  日期：2003.3

  Here, we report a novel strategy for the combinatorial or parallel solid-phase synthesis of potential inhibitors of the mur-pathway enzymes. The strategy involves the efficient use of p-alkoxybenzylidene acetal linker for reversible immobilization of sugar scaffolds to solid phase. This methodology was used to synthesize several glycopeptides on solid phase in good yields.

  在这里，我们报告了mur-途径酶的潜在抑制剂的组合或并行固相合成的新策略。该策略涉及有效使用对烷氧基亚苄基乙缩醛接头将糖支架可逆地固定到固相。该方法用于以良好的产率合成固相上的几种糖肽。
• A Total Synthesis of Arenastatin A, an Extremely Potent Cytotoxic Depsipeptide, from the Okinawan Marine Sponge Dysidea arenaria.
  作者：Motomasa KOBAYASHI、Michio KUROSU、Weiqi WANG、Isao KITAGAWA

  DOI：10.1248/cpb.42.2394

  日期：——

  An asymmetric synthesis of a cyclic depsipeptide arenastatin A (1), which was isolated from the marine sponge Dysidea arenaria and exhibited extremely potent cytotoxicity with IC50 5 pg/ml for KB cells, has been accomplished.

  一种不对称合成环状脱肽类化合物arenastatin A (1)的研究已完成，该化合物是从海绵Dysidea arenaria中分离得到的，并对KB细胞表现出极强的细胞毒性，其IC50为5 pg/ml。
• Enantioselective synthesis and stereochemical determination of the highly reduced polyketide ishigamide
  作者：Mitsuki Seo、Danyao Du、Yohei Katsuyama、Ryo Katsuta、Arata Yajima、Tomoo Nukada、Yasuo Ohnishi、Ken Ishigami

  DOI：10.1093/bbb/zbaa023

  日期：2021.1.7

  unsaturated fatty acid moiety has been confirmed in vitro to be synthesized by a type II PKS. Biosynthesis of such a highly reduced polyketide by a type II PKS is worthy of note. However, absolute configuration of ishigamide remained unknown. (R)-Ishigamide was synthesized enantioselectively employing Stille coupling and Wittig reaction between three units, vinyl iodide, stannyldienal, and Wittig salt. Stereochemistry

  Ishigamide 作为 Streptomyces sp. 重组菌株的代谢物被分离出来。MSC090213JE08 及其不饱和脂肪酸部分已在体外被证实是由 II 型 PKS 合成的。通过 II 型 PKS 生物合成这种高度还原的聚酮化合物值得注意。然而，ishigamide 的绝对构型仍然未知。(R)-Ishigamide 是采用Stille 偶联和三个单元、乙烯基碘、二甲锡二烯醛和Wittig 盐之间的Wittig 反应对映选择性合成的。与合成标准品相比，通过手性 HPLC 分析确定天然 ishigamide 的立体化学为 R。
• Scalable Solution-Phase Synthesis of the Biologically Active Cyclodepsipeptide Destruxin E, a Potent Negative Regulator of Osteoclast Morphology
  作者：Masahito Yoshida、Hiroshi Sato、Yoshitaka Ishida、Hiroshi Nakagawa、Takayuki Doi

  DOI：10.1021/jo402437z

  日期：2014.1.3

  The scalable solution-phase synthesis of the cyclodepsipeptide destruxin E (1) has been achieved. Diastereoselective dihydroxylation of the terminal alkene in a 2-alkoxy-4-pentenoic amide, 7, was successfully accomplished utilizing (DHQD)(2)PHAL as the chiral ligand, and it was found that the use of the L-proline moiety in the substrate as a chiral auxiliary was essential for the induction of high diastereoselectivity to afford the key compound 4 on a gram scale. MNBA-mediated macrolactonization of 3 was also performed without formation of the dimerized product even under higher-dilution conditions, and it is noteworthy that the internal hydrogen bonds and s-cis configuration of the amide bond between N-methylalanine and N-methylvaline in the cyclization precursor 3 would assist in the macrolactonization to provide the macrolactone 2 without forming a dimerized product. Finally, epoxide formation in the side chain afforded destruxin E (1) on a gram scale in high purity (>98%).
• The Absolute Stereostructure of Arenastatin A, a Potent Cytotoxic Depsipeptide from the Okinawan Marine Sponge Dysidea arenaria.
  作者：Motomasa KOBAYASHI、Michio KUROSU、Naoki OHYABU、Weiqi WANG、Satoshi FUJII、Isao KITAGAWA

  DOI：10.1248/cpb.42.2196

  日期：——

  The absolute stereostructure of arenastatin A (1), which was isolated from the Okinawan marine sponge Dysidea arenaria, has been determined on the bases of NMR and synthetic studies. Arenastatin A (1) is a cyclic depsipeptide exhibiting extremely potent cytotoxicity against KB cells with IC50 5pg/ml.

  根据核磁共振和合成研究，确定了从冲绳海洋海绵 Dysidea arenaria 中分离出来的阿那曲汀 A (1) 的绝对立体结构。阿仑他汀 A (1) 是一种环状去肽类化合物，对 KB 细胞具有极强的细胞毒性，IC50 为 5pg/ml 。