(2R,7S)-7-[(S)-3-Benzyloxy-1-(4-methoxy-benzyloxy)-propyl]-5-triethylsilanyl-2,3,6,7-tetrahydro-oxepine-2-carboxylic acid dimethylamide | 612050-83-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,7S)-7-[(S)-3-Benzyloxy-1-(4-methoxy-benzyloxy)-propyl]-5-triethylsilanyl-2,3,6,7-tetrahydro-oxepine-2-carboxylic acid dimethylamide
• 英文别名: (2R,7S)-7-[(1S)-1-[(4-methoxyphenyl)methoxy]-3-phenylmethoxypropyl]-N,N-dimethyl-5-triethylsilyl-2,3,6,7-tetrahydrooxepine-2-carboxamide
• CAS: 612050-83-6
• 化学式: C₃₃H₄₉NO₅Si
• 分子量: 567.841
• InChiKey: FOSUGQBRWMDALU-QAXCHELISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,7S)-7-[(S)-3-Benzyloxy-1-(4-methoxy-benzyloxy)-propyl]-5-triethylsilanyl-2,3,6,7-tetrahydro-oxepine-2-carboxylic acid dimethylamide 在 N-溴代丁二酰亚胺(NBS) 、 3-甲基-1-环己烯 、 四溴化碳 、 三辛基膦 、 potassium tert-butylate 、 三正丁基氢锡 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 alkaline aq. solution 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 8.67h， 生成 (S)-3-Benzyloxy-1-[(2S,7R)-7-((S)-1-bromo-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-propan-1-ol
  参考文献：
  名称：

  Total synthesis and determination of the absolute configuration of (+)-neoisoprelaurefucin

  摘要：

  The first total synthesis of the seven-membered ring ether marine natural product (+)-neoisoprelaurefucin (1) has been achieved employing a regioselective internal alkylation of amide 3, a novel sequence for removal of the triethylsilyl group from the resulting triethylsilyloxepene 2, and a bromoetherification of alcohol 16 as key steps. In addition, the absolute stereochemistry of the natural product was assigned. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0040-4039(03)01667-8
• 作为产物：
  描述：

  2-[(E)-(S)-1-[(S)-3-Benzyloxy-1-(4-methoxy-benzyloxy)-propyl]-5-(tetrahydro-pyran-2-yloxy)-3-triethylsilanyl-pent-3-enyloxy]-N,N-dimethyl-acetamide 在 四氯化碳 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 、 三苯基膦 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 1.33h， 生成 (2R,7S)-7-[(S)-3-Benzyloxy-1-(4-methoxy-benzyloxy)-propyl]-5-triethylsilanyl-2,3,6,7-tetrahydro-oxepine-2-carboxylic acid dimethylamide
  参考文献：
  名称：

  Total synthesis and determination of the absolute configuration of (+)-neoisoprelaurefucin

  摘要：

  The first total synthesis of the seven-membered ring ether marine natural product (+)-neoisoprelaurefucin (1) has been achieved employing a regioselective internal alkylation of amide 3, a novel sequence for removal of the triethylsilyl group from the resulting triethylsilyloxepene 2, and a bromoetherification of alcohol 16 as key steps. In addition, the absolute stereochemistry of the natural product was assigned. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0040-4039(03)01667-8

文献信息

• Total synthesis and determination of the absolute configuration of (+)-neoisoprelaurefucin
  作者：Hyunjoo Lee、Hyoungsu Kim、Seungyoup Baek、Sanghee Kim、Deukjoon Kim

  DOI：10.1016/s0040-4039(03)01667-8

  日期：2003.8

  The first total synthesis of the seven-membered ring ether marine natural product (+)-neoisoprelaurefucin (1) has been achieved employing a regioselective internal alkylation of amide 3, a novel sequence for removal of the triethylsilyl group from the resulting triethylsilyloxepene 2, and a bromoetherification of alcohol 16 as key steps. In addition, the absolute stereochemistry of the natural product was assigned. (C) 2003 Published by Elsevier Ltd.