tert-butyldimethylsilyl (2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-methyl-8,8,9,9-tetrachlorodecanoate | 159614-56-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyldimethylsilyl (2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-methyl-8,8,9,9-tetrachlorodecanoate
• 英文别名: [tert-butyl(dimethyl)silyl] (2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-8,8,9,9-tetrachloro-2-methyldecanoate
• CAS: 159614-56-9
• 化学式: C₂₃H₄₆Cl₄O₃Si₂
• 分子量: 568.599
• InChiKey: IGQCVZHSSBGVHP-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.49
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl (2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-methyl-8,8,9,9-tetrachlorodecanoate 在 sodium hydride 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 16.67h， 生成
  参考文献：
  名称：

  Mirabimide E, an Unusual N-Acylpyrrolinone from the Blue-Green Alga Scytonema mirabile: Structure Determination and Synthesis

  摘要：

  Mirabimide E, a solid tumor selective cytotoxin from the terrestrial blue-green alga Scytonema mirabile UH strain BY-8-1, possesses an unprecedented tetrachlorinated ethylene group and has been identified as (5S,2'R,3'R)-N- (anti-8/,8',9',9'-tetrachloro-3'-(carbamoyloxy)-2'-methyldecanoyl)-4-methoxy-5-methyl-3-pyrrolin-2-one. The total structure, including absolute stereochemistry, of this novel N-acylpyrrolinone was concluded from a combination of spectral and chemical studies, including stereoselective syntheses of three degradation products, viz. methyl (2R,3R)-anti-8,8,9,9-tetrachloro-3-hydroxy-2-methyldecanoate, (5R,6R)-trans-5-methyl-6-(5,5',6,6'-tetrachloroheptyl-1-oxa- 3-azacyclohexane-2,4-dione, and (5S)-4-methoxy-5-methyl-3-pyrrolin-2-one and the total synthesis of mirabimide E itself. The influence of the carbamate ester group on the chemical degradation and synthesis of mirabimide E is described.

  DOI：

  10.1021/ja00097a019
• 作为产物：
  描述：

  2-庚炔-1-醇 在 咪唑 、 sodium hydroxide 、 磺酰氯 、 potassium tert-butylate 、 四氯化钛 、 lithium 、 戴斯-马丁氧化剂 、 乙二胺 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 155.5h， 生成 tert-butyldimethylsilyl (2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-methyl-8,8,9,9-tetrachlorodecanoate
  参考文献：
  名称：

  Mirabimide E, an Unusual N-Acylpyrrolinone from the Blue-Green Alga Scytonema mirabile: Structure Determination and Synthesis

  摘要：

  Mirabimide E, a solid tumor selective cytotoxin from the terrestrial blue-green alga Scytonema mirabile UH strain BY-8-1, possesses an unprecedented tetrachlorinated ethylene group and has been identified as (5S,2'R,3'R)-N- (anti-8/,8',9',9'-tetrachloro-3'-(carbamoyloxy)-2'-methyldecanoyl)-4-methoxy-5-methyl-3-pyrrolin-2-one. The total structure, including absolute stereochemistry, of this novel N-acylpyrrolinone was concluded from a combination of spectral and chemical studies, including stereoselective syntheses of three degradation products, viz. methyl (2R,3R)-anti-8,8,9,9-tetrachloro-3-hydroxy-2-methyldecanoate, (5R,6R)-trans-5-methyl-6-(5,5',6,6'-tetrachloroheptyl-1-oxa- 3-azacyclohexane-2,4-dione, and (5S)-4-methoxy-5-methyl-3-pyrrolin-2-one and the total synthesis of mirabimide E itself. The influence of the carbamate ester group on the chemical degradation and synthesis of mirabimide E is described.

  DOI：

  10.1021/ja00097a019

文献信息

• Mirabimide E, an Unusual N-Acylpyrrolinone from the Blue-Green Alga Scytonema mirabile: Structure Determination and Synthesis
  作者：Seunguk Paik、Shmuel Carmeli、Jean Cullingham、Richard E. Moore、Gregory M. L. Patterson、Marcus A. Tius

  DOI：10.1021/ja00097a019

  日期：1994.9

  Mirabimide E, a solid tumor selective cytotoxin from the terrestrial blue-green alga Scytonema mirabile UH strain BY-8-1, possesses an unprecedented tetrachlorinated ethylene group and has been identified as (5S,2'R,3'R)-N- (anti-8/,8',9',9'-tetrachloro-3'-(carbamoyloxy)-2'-methyldecanoyl)-4-methoxy-5-methyl-3-pyrrolin-2-one. The total structure, including absolute stereochemistry, of this novel N-acylpyrrolinone was concluded from a combination of spectral and chemical studies, including stereoselective syntheses of three degradation products, viz. methyl (2R,3R)-anti-8,8,9,9-tetrachloro-3-hydroxy-2-methyldecanoate, (5R,6R)-trans-5-methyl-6-(5,5',6,6'-tetrachloroheptyl-1-oxa- 3-azacyclohexane-2,4-dione, and (5S)-4-methoxy-5-methyl-3-pyrrolin-2-one and the total synthesis of mirabimide E itself. The influence of the carbamate ester group on the chemical degradation and synthesis of mirabimide E is described.