(2R,3R)-3-tert-butyldimethylsilyloxy-1,2-epoxy-decane | 209479-91-4

• 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: (2R,3R)-3-tert-butyldimethylsilyloxy-1,2-epoxy-decane
• 英文别名: (2R,3R)-3-tert-butyldimethylsilyloxy-1,2-epoxydecane；tert-butyl-dimethyl-[(1R)-1-[(2R)-oxiran-2-yl]octoxy]silane
• CAS: 209479-91-4
• 化学式: C₁₆H₃₄O₂Si
• 分子量: 286.53
• InChiKey: SVVGECHXYUXCTJ-HUUCEWRRSA-N

物化性质

• 沸点：
  332.099±17.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.895±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-tert-butyldimethylsilyloxy-1,2-epoxy-decane 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 三氟化硼乙醚 、 盐酸羟胺 、 四丁基氟化铵 、 silver nitrate 、 乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 丙酮 为溶剂， 反应 8.17h， 生成 人参炔三醇
  参考文献：
  名称：

  Syntheses of two diastereoisomers of panaxytriol, a potent antitumor agent isolated from panax ginseng

  摘要：

  (3R, 9R, 10R) 和 (3R, 9S, 10S) 对映异构体 (2 和 3) 的PA3（panaxytriol）通过合成得到了，并确认了PA3的绝对构型为(3R, 9R, 10R)-heptadec-1-en-4,6-diyne-3,9,10-triol。 © 1999 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0040-4020(99)00352-x
• 作为产物：
  描述：

  2-癸炔-1-醇 在 Lindlar's catalyst 咪唑 、 喹啉 、 四氯化碳 、 Oxone 、 氢氧化钾 、 18-冠醚-6 、 Streptomyces sp. FCC₀₀₈ cells 、 Tris buffer 、 氢气 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 204.0h， 生成 (2R,3R)-3-tert-butyldimethylsilyloxy-1,2-epoxy-decane
  参考文献：
  名称：

  Chemoenzymatic Asymmetric Total Syntheses of Antitumor Agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng Using an Enantioconvergent Enzyme-Triggered Cascade Reaction

  摘要：

  Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantio-convergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.

  DOI：

  10.1021/jo020073w

文献信息

• Syntheses of two diastereoisomers of panaxytriol, a potent antitumor agent isolated from panax ginseng
  作者：Wei Lu、Guangrong Zheng、Daxin Gao、Junchao Cai

  DOI：10.1016/s0040-4020(99)00352-x

  日期：1999.6

  (3R, 9R, 10R) and (3R, 9S, 10S) diastereoisomers (2 and 3) of panaxytriol (1) were synthesized, and the absolute configuration of panaxytriol was confirmed as (3R, 9R, 10R)-heptadec-1-ene-4,6-diyne-3,9,10-triol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  (3R, 9R, 10R) 和 (3R, 9S, 10S) 对映异构体 (2 和 3) 的PA3（panaxytriol）通过合成得到了，并确认了PA3的绝对构型为(3R, 9R, 10R)-heptadec-1-en-4,6-diyne-3,9,10-triol。 © 1999 Elsevier Science Ltd. 保留所有权利。
• First Total Synthesis of Panaxytriol, a Potent Antitumor Agent Isolated from <i>Panax</i> <i>Ginseng</i>
  作者：Wei Lu、Guangrong Zheng、Junchao Cai

  DOI：10.1055/s-1998-1775

  日期：1998.7

  Panaxytriol 1, a potent antitumor agent isolated from Panax ginseng, was first synthesized, and its stereostructure was confirmed to be (3R,9R,10R)-heptadec-1-ene-4,6-diyne-3,9,10-triol.

  首次合成了从三七中分离出来的一种强效抗肿瘤药物--三七三醇 1，并确认其立体结构为 (3R,9R,10R)-十七碳-1-烯-4,6-二炔-3,9,10-三醇。
• Chemoenzymatic Asymmetric Total Syntheses of Antitumor Agents (3<i>R</i>,9<i>R</i>,10<i>R</i>)- and (3<i>S</i>,9<i>R</i>,10<i>R</i>)-Panaxytriol and (<i>R</i>)- and (<i>S</i>)-Falcarinol from <i>Panax </i><i>g</i><i>inseng</i> Using an Enantioconvergent Enzyme-Triggered Cascade Reaction
  作者：Sandra F. Mayer、Andreas Steinreiber、Romano V. A. Orru、Kurt Faber

  DOI：10.1021/jo020073w

  日期：2002.12.1

  Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantio-convergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.