(5-{(2,2-dimethyl-[1,3]dioxolan-4-yl)-[dimethyl(1,1,2-trimethylpropyl)silanyloxy]methyl}-thiazol-2-yl)carbamic acid tert-butyl ester | 458531-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (5-{(2,2-dimethyl-[1,3]dioxolan-4-yl)-[dimethyl(1,1,2-trimethylpropyl)silanyloxy]methyl}-thiazol-2-yl)carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[5-[(R)-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-1,3-thiazol-2-yl]carbamate
• CAS: 458531-09-4
• 化学式: C₂₂H₄₀N₂O₅SSi
• 分子量: 472.721
• InChiKey: JSGGCZLSWMOLOI-NVXWUHKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5-{(2,2-dimethyl-[1,3]dioxolan-4-yl)-[dimethyl(1,1,2-trimethylpropyl)silanyloxy]methyl}-thiazol-2-yl)carbamic acid tert-butyl ester 在 palladium on activated charcoal N-氯代丁二酰亚胺 、 sodium azide 、 氢气 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 4.0~80.0 ℃ 、101.33 kPa 条件下， 反应 180.0h， 生成 (5-{3-amino-2-chloro-1-[dimethyl(1,1,2-trimethylpropyl)silanyloxy]propyl}-thiazol-2-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of 5-deazathiogirollines: analogs of a natural antitumor agent

  摘要：

  2-Aminothiazole analogs of the natural antitumor agent, girolline, were prepared in natural stereochemistry series (threo) and in a non-natural series (erythro). The key-step involved a coupling reaction between 2,3-O-isopropylidene-D-glyceraldehyde and a properly protected 2-aminothiazole, via a dianion species, The biological activity of the prepared analogs was evaluated on human cancer cells to determine structure-activity relationship. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00383-6
• 作为产物：
  描述：

  噻唑-2-氨基甲酸叔丁酯 在 咪唑 、 正丁基锂 、 sodium methylate 、 二异丙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 (5-{(2,2-dimethyl-[1,3]dioxolan-4-yl)-[dimethyl(1,1,2-trimethylpropyl)silanyloxy]methyl}-thiazol-2-yl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of 5-deazathiogirollines: analogs of a natural antitumor agent

  摘要：

  2-Aminothiazole analogs of the natural antitumor agent, girolline, were prepared in natural stereochemistry series (threo) and in a non-natural series (erythro). The key-step involved a coupling reaction between 2,3-O-isopropylidene-D-glyceraldehyde and a properly protected 2-aminothiazole, via a dianion species, The biological activity of the prepared analogs was evaluated on human cancer cells to determine structure-activity relationship. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00383-6

文献信息

• Synthesis of 5-deazathiogirollines: analogs of a natural antitumor agent
  作者：Bruno Schiavi、Alain Ahond、Ali Al-Mourabit、Christiane Poupat、Angèle Chiaroni、Christiane Gaspard、Pierre Potier

  DOI：10.1016/s0040-4020(02)00383-6

  日期：2002.5

  2-Aminothiazole analogs of the natural antitumor agent, girolline, were prepared in natural stereochemistry series (threo) and in a non-natural series (erythro). The key-step involved a coupling reaction between 2,3-O-isopropylidene-D-glyceraldehyde and a properly protected 2-aminothiazole, via a dianion species, The biological activity of the prepared analogs was evaluated on human cancer cells to determine structure-activity relationship. (C) 2002 Elsevier Science Ltd. All rights reserved.