N-<(1R,2R)-2-hydroxycyclohexyl>valiolamine | 101540-73-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-<(1R,2R)-2-hydroxycyclohexyl>valiolamine
• 英文别名: 5-(2-Hydroxy-cyclohexylamino)-1-hydroxymethyl-cyclohexane-1,2,3,4-tetraol；(1S,2S,3R,4S,5S)-5-[[(1R,2R)-2-hydroxycyclohexyl]amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol
• CAS: 101540-73-2
• 化学式: C₁₃H₂₅NO₆
• 分子量: 291.345
• InChiKey: STUARDXZEPMAOG-QLHLUDRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  133
• 氢给体数：
  7
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2R,3S,4S,5S)-5-羟基-2,3,4-三(苄氧基)-5-[(苄氧基)甲基]-环己酮 在 甲酸 、 sodium cyanoborohydride 、 钯 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 10.0h， 生成 N-<(1R,2R)-2-hydroxycyclohexyl>valiolamine
  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

文献信息

• Synthesis and .alpha.-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents
  作者：Satoshi Horii、Hiroshi Fukase、Takao Matsuo、Yukihiko Kameda、Naoki Asano、Katsuhiko Matsui

  DOI：10.1021/jm00156a023

  日期：1986.6

  in this study have been found to be more potent than the corresponding N-substituted valienamine derivatives as well as the parent valiolamine. It is noteworthy that even simple N-substituted valiolamine derivatives such as N-[2-hydroxy-1-(hydroxymethyl)ethyl]-, N-[(1R,2R)-2-hydroxycyclohexyl]-, and N-[(R)-(-)-beta-hydroxyphenethyl]valiolamine (6, 8a, and 9a) have the stronger alpha-D-glucosidase inhibitory

  合成了各种N-取代的缬氨酰胺衍生物，包括化合物23a，24a和34a，其结构类似于天然存在的寡糖α-D-葡萄糖苷酶抑制剂的关键假二糖（25a和26a）。对猪蔗糖酶和麦芽糖酶的抑制活性。已经发现，在这项研究中评估的N-取代缬胺胺衍生物比相应的N-取代缬胺胺衍生物和母体缬胺胺更有效。值得注意的是，即使是简单的N-取代的缬胺胺衍生物，例如N- [2-羟基-1-（羟甲基）乙基]-，N-[（（1R，2R）-2-羟基环己基]-和N-[（R ）-（-）-β-羟基苯乙基]缬胺（6，8a，
• Synthesis of valiolamine and its N-substituted derivatives AO-128, validoxylamine G, and validamycin G via branched-chain inosose derivatives
  作者：Hiroshi Fukase、Satoshi Horii

  DOI：10.1021/jo00039a026

  日期：1992.6

  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.