(2R,3R)-3-Hydroxy-2-methoxy-4-methyl-pentanoic acid methoxy-methyl-amide | 185670-21-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-3-Hydroxy-2-methoxy-4-methyl-pentanoic acid methoxy-methyl-amide
• 英文别名: (2R,3R)-3-hydroxy-N,2-dimethoxy-N,4-dimethylpentanamide
• CAS: 185670-21-7
• 化学式: C₉H₁₉NO₄
• 分子量: 205.254
• InChiKey: JGSNDRJLCIAQHS-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-Hydroxy-2-methoxy-4-methyl-pentanoic acid methoxy-methyl-amide 、 生成 (S)-2-Methyl-2-triethylsilanyloxy-succinic acid 1-benzyl ester 4-{(R)-1-[(R)-methoxy-(methoxy-methyl-carbamoyl)-methyl]-2-methyl-propyl} ester
  参考文献：
  名称：

  The selective inhibition of phosphatases by natural toxins: the anhydride domain of tautomycin is not a primary factor in controlling PP1/PP2A selectivity

  摘要：

  Analogues of the potent and moderately selective PP1/PP2A inhibitor tautomycin (TM) were prepared with modifications in the C1'-C7' anhydride moiety. While all retain varying degrees of activity within a 3000-fold range of potencies, they also show remarkable constancy in their IC50 ratios, suggesting that the anhydride moiety is not critical in controlling the selectivity of inhibition. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00105-7
• 作为产物：
  描述：

  二甲羟胺盐酸盐 、 (R)-4-Benzyl-3-((2R,3R)-3-hydroxy-2-methoxy-4-methyl-pentanoyl)-oxazolidin-2-one 在 三甲基铝 作用下， 生成 (2R,3R)-3-Hydroxy-2-methoxy-4-methyl-pentanoic acid methoxy-methyl-amide
  参考文献：
  名称：

  丝氨酸/苏氨酸特异性蛋白磷酸酶抑制剂互变霉素的全合成（1）。

  摘要：

  描述了蛋白质磷酸酶抑制剂互变霉素的收敛，不对称合成。天然产物是通过在C21-C22键处连接两个相当复杂的主要片段而构建的。C 1 -C 21酮的绝对立体化学源自（S）-香茅烯和（2R，3S）-香叶醇环氧化物。用Duthaler的手性丙酸钛烯醇酯介绍了C6-C7和C18-C19的抗立体化学关系。使用Evan的恶唑烷酮手性助剂建立了C13-C14和C23-C24的顺式立体化学关系。通过以丙酮N，N-二甲基hydr为中心关键的一锅双烷基化-螺环化序列有效地构建了螺酮。

  DOI：

  10.1021/jo961633s

文献信息

• Total Synthesis of the Serine/Threonine-Specific Protein Phosphatase Inhibitor Tautomycin¹
  作者：James E. Sheppeck、Wen Liu、A. Richard Chamberlin

  DOI：10.1021/jo961633s

  日期：1997.1.1

  A convergent, asymmetric synthesis of the protein phosphatase inhibitor, tautomycin, is described. The natural product was constructed by joining two major fragments of comparable complexity at the C21-C22 bond. Absolute stereochemistry of the C1-C21 ketone originates from (S)-citronellene and (2R,3S)-geraniol epoxide. The anti stereochemical relationships at C6-C7 and C18-C19 were introduced with

  描述了蛋白质磷酸酶抑制剂互变霉素的收敛，不对称合成。天然产物是通过在C21-C22键处连接两个相当复杂的主要片段而构建的。C 1 -C 21酮的绝对立体化学源自（S）-香茅烯和（2R，3S）-香叶醇环氧化物。用Duthaler的手性丙酸钛烯醇酯介绍了C6-C7和C18-C19的抗立体化学关系。使用Evan的恶唑烷酮手性助剂建立了C13-C14和C23-C24的顺式立体化学关系。通过以丙酮N，N-二甲基hydr为中心关键的一锅双烷基化-螺环化序列有效地构建了螺酮。
• The selective inhibition of phosphatases by natural toxins: the anhydride domain of tautomycin is not a primary factor in controlling PP1/PP2A selectivity
  作者：Wen Liu、James E. Sheppeck、David A. Colby、Hsien-Bin Huang、Angus C. Nairn、A.Richard Chamberlin

  DOI：10.1016/s0960-894x(03)00105-7

  日期：2003.5

  Analogues of the potent and moderately selective PP1/PP2A inhibitor tautomycin (TM) were prepared with modifications in the C1'-C7' anhydride moiety. While all retain varying degrees of activity within a 3000-fold range of potencies, they also show remarkable constancy in their IC50 ratios, suggesting that the anhydride moiety is not critical in controlling the selectivity of inhibition. (C) 2003 Elsevier Science Ltd. All rights reserved.