rac-((((3S,4S)-3,4-dimethyltetrahydrofuran-2,2-diyl)bis(2,6-dimethoxy-4,1-phenylene))bis(oxy))bis(tert-butyldimethylsilane)

• 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: rac-((((3S,4S)-3,4-dimethyltetrahydrofuran-2,2-diyl)bis(2,6-dimethoxy-4,1-phenylene))bis(oxy))bis(tert-butyldimethylsilane)
• 英文别名: tert-butyl-[4-[(3R,4R)-2-[4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethoxyphenyl]-3,4-dimethyloxolan-2-yl]-2,6-dimethoxyphenoxy]-dimethylsilane
• 化学式: C₃₄H₅₆O₇Si₂
• 分子量: 632.985
• InChiKey: ZWZDPIDPYRPUFQ-XZOQPEGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.04
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  rac-((((3S,4S)-3,4-dimethyltetrahydrofuran-2,2-diyl)bis(2,6-dimethoxy-4,1-phenylene))bis(oxy))bis(tert-butyldimethylsilane) 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以96%的产率得到(±)-scidumlignan D
  参考文献：
  名称：

  Total Synthesis of (−)-Sacidumlignans B and D

  摘要：

  The first total synthesis of naturally occurring sacidumlignans A (1), B (2), and D (4) was executed and the absolute configuration of 2 and 4 was determined. A diastereoselective alpha- methylation of a lactone was used as the key step for the control of the chiral centers of the central lignan core. An acid mediated dehydrative cyclization of an aldehyde to construct the dihydronaphthalene unit of 2 and the aromatization of the intermediate dihydronaphthalene derivative to synthesize 1 are the key reactions employed in this regard.

  DOI：

  10.1021/jo2021696
• 作为产物：
  描述：

  5,5-bis(4-(tert-butyldimethylsilyloxy)-3,5-dimethoxyphenyl)-4-methyldihydrofuran-2(3H)-one 在 lithium aluminium tetrahydride 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.08h， 生成 rac-((((3S,4S)-3,4-dimethyltetrahydrofuran-2,2-diyl)bis(2,6-dimethoxy-4,1-phenylene))bis(oxy))bis(tert-butyldimethylsilane)
  参考文献：
  名称：

  Total Synthesis of (±)-Sacidumlignan D

  摘要：

  The first total synthesis of (+/-)-sacidumlignan D featuring a Zn-mediated Barbier reaction and reverse Wacker oxidation to form the key gamma-lactone, its diastereoselective alpha-methylation followed by reduction cyclization, was documented.

  DOI：

  10.1021/jo1025749

文献信息

• Total Synthesis of (−)-Sacidumlignans B and D
  作者：Jeetendra Kumar Rout、C. V. Ramana

  DOI：10.1021/jo2021696

  日期：2012.2.3

  The first total synthesis of naturally occurring sacidumlignans A (1), B (2), and D (4) was executed and the absolute configuration of 2 and 4 was determined. A diastereoselective alpha- methylation of a lactone was used as the key step for the control of the chiral centers of the central lignan core. An acid mediated dehydrative cyclization of an aldehyde to construct the dihydronaphthalene unit of 2 and the aromatization of the intermediate dihydronaphthalene derivative to synthesize 1 are the key reactions employed in this regard.
• Total Synthesis of (±)-Sacidumlignan D
  作者：Sunil Kumar Pandey、C. V. Ramana

  DOI：10.1021/jo1025749

  日期：2011.4.1

  The first total synthesis of (+/-)-sacidumlignan D featuring a Zn-mediated Barbier reaction and reverse Wacker oxidation to form the key gamma-lactone, its diastereoselective alpha-methylation followed by reduction cyclization, was documented.