(3R,4S)-4-amino-3-methoxy-2-methylhept-6-en-2-ol | 1309369-11-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S)-4-amino-3-methoxy-2-methylhept-6-en-2-ol
• CAS: 1309369-11-6
• 化学式: C₉H₁₉NO₂
• 分子量: 173.255
• InChiKey: REXWYKBXMYNFCQ-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-amino-3-methoxy-2-methylhept-6-en-2-ol 在 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 12.0h， 生成 N-(6-hydroxy-3-methoxy-2,2-dimethyltetrahydro-2H-pyran-4-yl)benzamide
  参考文献：
  名称：

  Concise and divergent approach to 3-O-acyl-l-noviose derivatives and their 3-amino bioisosteres: 3-O-benzoyl-l-noviose and N-benzoyl-3-amino-l-noviose

  摘要：

  Generally applicable concise approaches to 3-O-acyl-L-noviose derivatives and their 3-amino bioisosteres, represented by 5 and 6, were described. Chiral aldehyde 7 was thus prepared from dimethyl L-tartrate in five steps, and converted into 5 and 6 by employing substrate induced asymmetric aldehyde or N-sulfinyl aldimine allylation and dihydropyrane epoxidation as key steps, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.092
• 作为产物：
  描述：

  (3R,4R)-4-methoxy-2,5-dimethylhexane-2,3,5-triol 在 盐酸 、 甲醇 、 sodium periodate 、 copper(II) sulfate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 30.5h， 生成 (3R,4S)-4-amino-3-methoxy-2-methylhept-6-en-2-ol
  参考文献：
  名称：

  Concise and divergent approach to 3-O-acyl-l-noviose derivatives and their 3-amino bioisosteres: 3-O-benzoyl-l-noviose and N-benzoyl-3-amino-l-noviose

  摘要：

  Generally applicable concise approaches to 3-O-acyl-L-noviose derivatives and their 3-amino bioisosteres, represented by 5 and 6, were described. Chiral aldehyde 7 was thus prepared from dimethyl L-tartrate in five steps, and converted into 5 and 6 by employing substrate induced asymmetric aldehyde or N-sulfinyl aldimine allylation and dihydropyrane epoxidation as key steps, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.092

文献信息

• Simplified aminocoumarin analogues as anticancer agents: Amino isosteric replacement in the noviose moiety resulted in substantial enhancement of antiproliferative activity
  作者：Ting Zhang、Zheng Yan、Yun-Feng Li、Nan Wang

  DOI：10.1016/j.cclet.2013.04.046

  日期：2013.8

  Simplified aminocoumarin analogues, either noviosylated or simple basic heterocycle attached 3-amidocoumarin compounds, are known to be promising anticancer agents targeting the C-terminal ATP-binding site of Hsp90. In this study, 3'-amino isosteric replacement in the noviose moiety of two known noviose containing Hsp90 C-terminal inhibitors was synthetically realized for the first time. In vitro evaluation of these compounds suggested that the introduction of a basic amino group into the noviose subunit resulted in significant improvement of their cytotoxicities. (C) 2013 Yun-Feng Li and Nan Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.