methyl (2E,6E,10E,14E)-geranylfarnesoate | 76235-32-0

• 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: methyl (2E,6E,10E,14E)-geranylfarnesoate
• 英文别名: 2-acetamido-1,3,4-tri-O-acetyl-2,6-dideoxy-6-iodo-α-D-glucopyranose；2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-6-iodo-α-D-glucopyranose；6-Deoxy-6-jod-1,3,4-tri-O-acetyl-N-acetyl-α-D-glucosamin；6-Deoxy-6-jod-tetraacetyl-α-D-glucopyranosamin
• CAS: 76235-32-0
• 化学式: C₁₄H₂₀INO₈
• 分子量: 457.219
• InChiKey: ZDCLNNXMNOQRSA-KSTCHIGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.08
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  117.23
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl (2E,6E,10E,14E)-geranylfarnesoate 在 溴 、 sodium ethanolate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 0.53h， 生成 2-acetamido-2-deoxy-6-S-dimethylarsino-6-thio-α-D-glucopyranose
  参考文献：
  名称：

  Chen; Banks; Irgolic, Journal of the Chemical Society. Perkin transactions I, 1980, vol. 10, p. 2287 - 2293

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Acetamido-1,3,4-tri-O-acetyl-2-deoxy-6-O-tosyl-D-glucopyranose 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以87.8%的产率得到methyl (2E,6E,10E,14E)-geranylfarnesoate
  参考文献：
  名称：

  Synthesis of new sugar derivatives and evaluation of their antibacterial activities against Mycobacterium tuberculosis

  摘要：

  A series of sugar derivatives (1-13) were synthesized and evaluated for antibacterial activity against Mycobacterium tuberculosis (MTB), especially multi-drug resistant (MDR) MTB, and the structure-activity relationships of these compounds were studied. The results showed that the compound OCT313 (2-acetamido-2deoxy-beta-D-glucopyranosyl N,N-dimethyldithiocarbamate) (4) exhibited significant in vitro bactericidal activity, and that the dithiocarbamate group at C-1 position of the glucopyranoside ring was requisite for the antibacterial activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.095

文献信息

• Vitamin B12 Catalysis of Zinc-Mediated 6-Deoxy-6-iodopyranoside Fragmentation: A Mild and Convenient Preparation of ω-Unsaturated Hexose Derivatives (5-Hexenoses)
  作者：Martin Kleban、Ulrich Kautz、Jörg Greul、Petra Hilgers、Rolf Kugler、Han-Qing Dong、Volker Jäger

  DOI：10.1055/s-2000-6305

  日期：——

  The known zinc-mediated preparation of 5-hexenoses by fragmentation of 6-iodopyranosides can be performed in a simple, fast, and mild way, with less side reactions, when vitamin B12 is employed as a catalyst.

  已知的通过6-碘吡喃糖苷断裂合成5-己烯糖的锌介导方法，在维生素B12用作催化剂时，可以以简单、快速和温和的方式进行，且副反应较少。