tert-butyl allyl-(3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methylthiazol-4-yl)-pent-4-enyl)carbamate | 1054315-68-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl allyl-(3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methylthiazol-4-yl)-pent-4-enyl)carbamate
• CAS: 1054315-68-2
• 化学式: C₂₄H₄₂N₂O₃SSi
• 分子量: 466.761
• InChiKey: ZWQJOEOKJFBDSA-LAYTVVDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  51.66
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl allyl-(3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methylthiazol-4-yl)-pent-4-enyl)carbamate 在 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以81%的产率得到tert-butyl allyl-(3-hydroxy-4-methyl-5-(2-methylthiazol-4-yl)-pent-4-enyl)carbamate
  参考文献：
  名称：

  Synthesis of 12-aza analogs of epothilones and (E)-9,10-dehydroepothilones

  摘要：

  N-Boc-12-aza-epothilone analog (azathilone) 1 is a potent inhibitor of human cancer cell growth and represents a structurally new class of natural product-derived microtubule-stabilizing agents. Compound 1 has been prepared employing a convergent strategy that is based on the consecutive assembly of building blocks 3, 4, and 19 into diene 20 and subsequent RCM-mediated macrocycle formation. The aldol reaction between aldehyde 3 and ketone 4 delivered the required 6R,7S diastereoisomer 5 with good selectivity and provided a reliable entry into the stereoselective synthesis of carboxylic acid 12. RCM with diene 20 was highly E-selective, thus giving efficient access to (E)-9,10-dehydro-1 (2). The latter is a key analog in SAR studies with 1. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.017
• 作为产物：
  描述：

  (S,E)-N-allyl-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methylthiazol-4-yl)-pent-4-en-1-amine 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以92%的产率得到tert-butyl allyl-(3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methylthiazol-4-yl)-pent-4-enyl)carbamate
  参考文献：
  名称：

  Synthesis of 12-aza analogs of epothilones and (E)-9,10-dehydroepothilones

  摘要：

  N-Boc-12-aza-epothilone analog (azathilone) 1 is a potent inhibitor of human cancer cell growth and represents a structurally new class of natural product-derived microtubule-stabilizing agents. Compound 1 has been prepared employing a convergent strategy that is based on the consecutive assembly of building blocks 3, 4, and 19 into diene 20 and subsequent RCM-mediated macrocycle formation. The aldol reaction between aldehyde 3 and ketone 4 delivered the required 6R,7S diastereoisomer 5 with good selectivity and provided a reliable entry into the stereoselective synthesis of carboxylic acid 12. RCM with diene 20 was highly E-selective, thus giving efficient access to (E)-9,10-dehydro-1 (2). The latter is a key analog in SAR studies with 1. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.017