bisdethiobis(methylthio)acetylaranotin | 20485-02-3

• 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: bisdethiobis(methylthio)acetylaranotin
• 英文别名: Didethiodi(methylthio)acetylaranotin；[(1R,4S,5S,12R,15S,16S)-16-acetyloxy-1,12-bis(methylsulfanyl)-2,13-dioxo-8,19-dioxa-3,14-diazapentacyclo[12.8.0.03,12.04,10.015,21]docosa-6,9,17,20-tetraen-5-yl] acetate
• CAS: 20485-02-3
• 化学式: C₂₄H₂₆N₂O₈S₂
• 分子量: 534.611
• InChiKey: MNIWVYZRLOFLBX-KHTMQFLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  162
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  bisdethiobis(methylthio)acetylaranotin 在 4-二甲氨基吡啶 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  半合成的（-）-SCH 64874和Hirsutellomycin的结构测定

  摘要：

  通过半合成确定C 2对称的表二硫代二酮哌嗪生物碱SCH 64874的结构。通过比较四个可能的非对映异构的β-羟基羧酸片段与SCH 64874的NMR数据，可以确定具有三个手性中心的β-羟基羧酸链的相对立体化学。两种对映体的β-羟基羧酸揭示了SCH 64874的相对立体化学。以逐步方式确定了类似生物碱hirsutellomycin的β-酮羧酸链的相对立体化学。该C4'-C6' SYN通过将相应酯片段的NMR数据与hirsutellomycin的NMR数据进行比较，可以预测二者之间的相关性。整个分子的相对立体化学，包括可差向异构的C2'立体中心，是通过将四个可能的侧链引入双脱硫基二（甲硫基）脱乙酰基花生四烯酸核心来确定的。我们发现，C2'的立体化学与受核心结构影响的热力学稳定形式的立体化学趋同。

  DOI：

  10.1021/acs.joc.6b02452
• 作为产物：
  描述：

  alternarosin A 、 乙酸酐 以 吡啶 为溶剂， 以1.8 mg的产率得到bisdethiobis(methylthio)acetylaranotin
  参考文献：
  名称：

  Cerebrosides of the Halotolerant Fungus Alternaria raphani Isolated from a Sea Salt Field

  摘要：

  In order to search for structurally novel and bioactive natural compounds from marine-derived fungi, a halotolerant fungal strain (THW-18) identified as Alternaria raphani was isolated from sediment collected in the Hongdao sea salt field. From the ethyl acetate extract of Alteniaria raphani, three new cerebrosides, alternarosides A-C (1-3), and a new diketopiperazine alkaloid, alternarosin A (4), together with 15 known compounds were isolated and identified by spectroscopic and chemical methods, as well as X-ray crystal diffraction analysis. Compounds 1-4 showed weak antibacterial activity against Escherichia coli, Bacillus subtilis, and Candida albicans with MIC values ranging from 70 to 400 mu M..

  DOI：

  10.1021/np9002299

文献信息

• Structural Determination of (−)-SCH 64874 and Hirsutellomycin by Semisynthesis
  作者：Hidetoshi Tokuyama、Kaori Yamada、Hideto Fujiwara、Juri Sakata、Kentaro Okano、Malipan Sappan、Masahiko Isaka

  DOI：10.1021/acs.joc.6b02452

  日期：2017.1.6

  relative stereochemistry of the β-keto carboxylic acid chain of the analogous alkaloid hirsutellomycin was determined in a stepwise manner. The C4′–C6′ syn relationships were predicted by comparing the NMR data of the corresponding ester fragments with that of hirsutellomycin. The relative stereochemistry of the whole molecule, including the epimerizable C2′ stereocenter, was determined by introduction

  通过半合成确定C 2对称的表二硫代二酮哌嗪生物碱SCH 64874的结构。通过比较四个可能的非对映异构的β-羟基羧酸片段与SCH 64874的NMR数据，可以确定具有三个手性中心的β-羟基羧酸链的相对立体化学。两种对映体的β-羟基羧酸揭示了SCH 64874的相对立体化学。以逐步方式确定了类似生物碱hirsutellomycin的β-酮羧酸链的相对立体化学。该C4'-C6' SYN通过将相应酯片段的NMR数据与hirsutellomycin的NMR数据进行比较，可以预测二者之间的相关性。整个分子的相对立体化学，包括可差向异构的C2'立体中心，是通过将四个可能的侧链引入双脱硫基二（甲硫基）脱乙酰基花生四烯酸核心来确定的。我们发现，C2'的立体化学与受核心结构影响的热力学稳定形式的立体化学趋同。
• Cerebrosides of the Halotolerant Fungus <i>Alternaria raphani</i> Isolated from a Sea Salt Field
  作者：Wenliang Wang、Yi Wang、Hongwen Tao、Xiaoping Peng、Peipei Liu、Weiming Zhu

  DOI：10.1021/np9002299

  日期：2009.9.25

  In order to search for structurally novel and bioactive natural compounds from marine-derived fungi, a halotolerant fungal strain (THW-18) identified as Alternaria raphani was isolated from sediment collected in the Hongdao sea salt field. From the ethyl acetate extract of Alteniaria raphani, three new cerebrosides, alternarosides A-C (1-3), and a new diketopiperazine alkaloid, alternarosin A (4), together with 15 known compounds were isolated and identified by spectroscopic and chemical methods, as well as X-ray crystal diffraction analysis. Compounds 1-4 showed weak antibacterial activity against Escherichia coli, Bacillus subtilis, and Candida albicans with MIC values ranging from 70 to 400 mu M..