tetra-O-benzyl-N-phthaloylvalienamine | 140926-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: tetra-O-benzyl-N-phthaloylvalienamine
• 英文别名: 2-[(1S,4R,5S,6S)-4,5,6-tris(phenylmethoxy)-3-(phenylmethoxymethyl)cyclohex-2-en-1-yl]isoindole-1,3-dione
• CAS: 140926-88-1
• 化学式: C₄₃H₃₉NO₆
• 分子量: 665.786
• InChiKey: YISSHHZWFNKWDE-XRFUAQTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.56
• 重原子数：
  50.0
• 可旋转键数：
  14.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tetra-O-benzyl-N-phthaloylvalienamine 在 一水合肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以74%的产率得到Tetra-O-benzylvalienamine
  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
• 作为产物：
  描述：

  (3S,4S,5R,6R)-1-dimethoxyphosphoryl-3,4,5,7-tetrakis(phenylmethoxy)heptane-2,6-diol 在 sodium tetrahydroborate 、 cerium(III) chloride 、 18-冠醚-6 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 三氟乙酸酐 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 29.0h， 生成 tetra-O-benzyl-N-phthaloylvalienamine
  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