Validamycin G | 106054-17-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Validamycin G
• 英文别名: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(1S,2S,4S,5S,6R)-2,5,6-trihydroxy-2-(hydroxymethyl)-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]cyclohexyl]oxyoxane-3,4,5-triol
• CAS: 106054-17-5
• 化学式: C₂₀H₃₅NO₁₄
• 分子量: 513.496
• InChiKey: FKVLATUQODRNIC-ZFNZPGKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.3
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  273
• 氢给体数：
  13
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Validamycin G 在 氧化铂 水 、 氨 、 硫酸 作用下， 反应 10.0h， 以to give a white powder of valiolamine (11 mg)的产率得到井冈霉醇胺
  参考文献：
  名称：

  Valiolamine derivatives and production thereof

  摘要：

  公式（I）的新型valiolamine衍生物：##STR1## 其中R代表氢或β-D-葡萄糖吡喃糖基，可用作valiolamine的起始材料，可转化为更有效的α-葡萄糖苷酶抑制剂化合物。通过在培养基中培养水解链霉菌并从培养液中回收产生和积累的valiolamine衍生物来获得该valiolamine衍生物。

  公开号：

  US04923975A1
• 作为产物：
  描述：

  (1S,2S,3R,4S,5S)-3,4-Bis-benzyloxy-1-benzyloxymethyl-5-((1S,4R,5S,6S)-4,5,6-tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexanol 在 氨 、 sodium 作用下， 反应 1.0h， 以6%的产率得到Validamycin G
  参考文献：
  名称：

  Synthesis of valiolamine and its N-substituted derivatives AO-128, validoxylamine G, and validamycin G via branched-chain inosose derivatives

  摘要：

  Novel synthetic routes to valiolamine (1a) and N-substituted valiolamine derivatives via branched-chain inosose derivatives are described. (1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-[(benzyloxy)methyl]-5-oxo-1,2,3,4-cyclohexanetetrol (3), a branched-chain inosose derivative prepared from D-glucose, 2 has been converted into 1a via the ketoxime 7 followed by hydrogenation. N-Substituted valiolamine derivatives having strong alpha-D-glucosidase inhibitory activity have been synthesized by the direct reductive amination of the branched-chain inosose derivative 3 with an appropriate amino compound to construct the N-substituent moiety, followed by removal of the O-benzyl protecting group. The stereoselective preparation of two representative derivatives, N-[2-hydroxy-1-(hydroxymethyl)ethyl]valiolamine (2a, AO-128)3 and N-[1R,2R)-2-hydroxyclohexyl]valiolamine (2b)3 is described. Application of branched-chain inosose derivatives 3 and 23 to the total synthesis of natural N-substituted valiolamine derivatives validoxylamine G (5a) and validamycin G (6a) is also described.

  DOI：

  10.1021/jo00039a026