ent-16β-hydroxybeyeran-19-oic acid methyl ester | 30217-45-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ent-16β-hydroxybeyeran-19-oic acid methyl ester
• 英文别名: Methyl 16-hydroxystachan-18-oate；methyl (1R,4S,5R,9S,13S,14R)-14-hydroxy-5,9,13-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 30217-45-9
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: LYFJGTIFFFMUCR-OATJNCPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ent-16β-hydroxybeyeran-19-oic acid methyl ester 在 2,6-二甲基吡啶 、 氢氧化钾 、 三氟化硼乙醚 、 lithium iodide 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Design and synthesis of an α-mannosyl terpenoid as selective inhibitor of P-selectin

  摘要：

  In an effort to develop the structural and functional mimics of the tetrasaccharide sialyl Lewis x as selective inhibitors of P-selectin, we have designed a mannosyl terpenoid derivative that selectively inhibits P-selectin with an IC50 value of 60 mu M, but exhibits no inhibition activity against E- and L-selectins. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10022-1
• 作为产物：
  描述：

  异甜菊醇 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 ent-16β-hydroxybeyeran-19-oic acid methyl ester
  参考文献：
  名称：

  Structural modifications of isosteviol. Partial synthesis of atiserene and isoatiserene

  摘要：

  DOI：

  10.1021/jo00817a014

文献信息

• The biotransformation of some ent-beyeran-19-oic acids by Gibberella fujikuroi
  作者：Mohammad Shaiq Ali、James R. Hanson、Bras H. de Oliveira

  DOI：10.1016/0031-9422(92)90026-m

  日期：1992.2

  ent -beyeran-19-oic acid), ent -16β-hydroxybeyeran-19-oic acid, and ent -16β-hydroxy-16α-methylbeyeran-19-oic acid by Gibberella fujikuroi has been shown to give ring A desoxybeyergibberellin analogues of GA 9 , GA 12 and GA 25 . The ent -16β-hydroxybeyeran-19-oic acid also gave some hydroxylated beyeranes and the 7β-hydroxybeyeranolide.

  摘要 藤黑赤霉对异甜菊酸 (ent -beyeran-19-oic acid)、ent -16β-hydroxybeyeran-19-oic acid 和 ent -16β-hydroxy-16α-methylbeyeran-19-oic acid 的生物转化已被证明是得到 GA 9 、GA 12 和 GA 25 的环 A 脱氧拜耳赤霉素类似物。ent -16β-hydroxybeyeran-19-oic acid 也产生了一些羟基化的 beyeranes 和 7β-hydroxybeyeranolide。
• The chemistry of the tetracyclic diterpenoids—V
  作者：J.R. Hanson

  DOI：10.1016/0040-4020(67)85025-7

  日期：1967.1

  Detailed evidence for the interrelationship between monogynol and steviol and the reverse conversion of the stachene skeleton to the kaurene skeleton is presented. The preparation of stach-15-en-2-one is also described.

  提出了有关甘油一丁香酚和甜菊醇之间相互关系以及将斯塔克烯骨架反向转化为贝壳杉烯骨架的详细证据。还描述了stach-15-en-2-one的制备。
• Structural modifications of isosteviol. Partial synthesis of atiserene and isoatiserene
  作者：Robert M. Coates、Edward F. Bertram

  DOI：10.1021/jo00817a014

  日期：1971.9
• Design and synthesis of an α-mannosyl terpenoid as selective inhibitor of P-selectin
  作者：Tsuyoshi Ikeda、Tetsuya Kajimoto、Hirosato Kondo、Chi-Huey Wong

  DOI：10.1016/s0960-894x(97)10022-1

  日期：1997.10

  In an effort to develop the structural and functional mimics of the tetrasaccharide sialyl Lewis x as selective inhibitors of P-selectin, we have designed a mannosyl terpenoid derivative that selectively inhibits P-selectin with an IC50 value of 60 mu M, but exhibits no inhibition activity against E- and L-selectins. (C) 1997 Elsevier Science Ltd.