(1R,2R)-1-(2,4-bis(benzyloxy)-6-chloro-5-phenylpyridin-3-yl)-2-methylbut-3-en-1-ol | 1353390-17-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (1R,2R)-1-(2,4-bis(benzyloxy)-6-chloro-5-phenylpyridin-3-yl)-2-methylbut-3-en-1-ol
• 英文别名: (1R,2R)-1-[6-chloro-5-phenyl-2,4-bis(phenylmethoxy)pyridin-3-yl]-2-methylbut-3-en-1-ol
• CAS: 1353390-17-6
• 化学式: C₃₀H₂₈ClNO₃
• 分子量: 486.01
• InChiKey: LTMSQHOHKVRFEW-JIPXPUAJSA-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：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  51.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-(2,4-bis(benzyloxy)-6-chloro-5-phenylpyridin-3-yl)-2-methylbut-3-en-1-ol 在 Grubbs catalyst first generation sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-chloro-5-[(2R,3R)-3-methyl-5-[(1E,6E)-6-methylocta-1,6-dienyl]-3,6-dihydro-2H-pyran-2-yl]-3-phenyl-4,6-bis(phenylmethoxy)pyridine
  参考文献：
  名称：

  New strategy for the synthesis of phosphatase inhibitors TMC-69-6H and analogs

  摘要：

  An efficient method for the synthesis of antitumor TMC-69-6H and related analogs which have been demonstrated to be phosphatase (PTP1B, VHR, and PP1) inhibitors, is reported. This strategy involves two key steps: a diastereoselective aldol reaction and a one-pot tandem ring-closing and cross metathesis for the construction of the pyran moiety. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.102
• 作为产物：
  描述：

  6-chloro-4-hydroxy-2-oxo-5-phenyl-1,2-dihydropyridine-3-carbaldehyde 在 potassium carbonate 、 L-脯氨酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 75.0h， 生成 (1R,2R)-1-(2,4-bis(benzyloxy)-6-chloro-5-phenylpyridin-3-yl)-2-methylbut-3-en-1-ol
  参考文献：
  名称：

  Formal synthesis of TMC-69-6H via a one-pot enantioselective domino proline-mediated aldol/olefin homologation procedure

  摘要：

  Enantioselective synthesis of TMC-69-6H was accomplished from readily accessible pyridone derivative via a domino proline-mediated aldol reaction/olefin homologation, followed by tandem ring-closing and cross metathesis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.025

文献信息

• Formal synthesis of TMC-69-6H via a one-pot enantioselective domino proline-mediated aldol/olefin homologation procedure
  作者：Sophie Vuong、Nicolas Brondel、Christophe Len、Sébastien Papot、Brigitte Renoux

  DOI：10.1016/j.tet.2011.11.025

  日期：2012.1

  Enantioselective synthesis of TMC-69-6H was accomplished from readily accessible pyridone derivative via a domino proline-mediated aldol reaction/olefin homologation, followed by tandem ring-closing and cross metathesis. (C) 2011 Elsevier Ltd. All rights reserved.
• New strategy for the synthesis of phosphatase inhibitors TMC-69-6H and analogs
  作者：Nicolas Brondel、Brigitte Renoux、Jean-Pierre Gesson

  DOI：10.1016/j.tetlet.2006.10.102

  日期：2006.12

  An efficient method for the synthesis of antitumor TMC-69-6H and related analogs which have been demonstrated to be phosphatase (PTP1B, VHR, and PP1) inhibitors, is reported. This strategy involves two key steps: a diastereoselective aldol reaction and a one-pot tandem ring-closing and cross metathesis for the construction of the pyran moiety. (c) 2006 Elsevier Ltd. All rights reserved.