(3R,5S)-5-[(S)-2,2,3,3,10,10-hexamethyl-9,9-diphenyl-4,8-dioxa-3,9-disilaundecan-5-yl]-3-methyldihydrofuran-2(3H)-one | 1015071-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,5S)-5-[(S)-2,2,3,3,10,10-hexamethyl-9,9-diphenyl-4,8-dioxa-3,9-disilaundecan-5-yl]-3-methyldihydrofuran-2(3H)-one
• 英文别名: (3R,5S,1'S)-5-[1-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)propyl]-3-methyldihydrofuran-2-one；(3R,5S)-5-[1-(S)-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)propyl]-3-methyldihydrofuran-2-one；(3R,5S)-5-[(1S)-1-[tert-butyl(dimethyl)silyl]oxy-3-[tert-butyl(diphenyl)silyl]oxypropyl]-3-methyloxolan-2-one
• CAS: 1015071-58-5
• 化学式: C₃₀H₄₆O₄Si₂
• 分子量: 526.864
• InChiKey: HUTRRDFLWHBWKM-NPAAKHOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,5S)-5-[(S)-2,2,3,3,10,10-hexamethyl-9,9-diphenyl-4,8-dioxa-3,9-disilaundecan-5-yl]-3-methyldihydrofuran-2(3H)-one 在 氟化铵 、 锂硼氢 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 37.0h， 生成 (S)-3-(tert-butyldimethylsilyloxy)-3-[(4S,6R)-2,2,6-trimethyl-1,3-dioxepan-4-yl]propan-1-ol
  参考文献：
  名称：

  Stereoselective Synthesis of the C10-C18 Fragment of Iriomoteolide-3a

  摘要：

  An efficient synthesis of the highly stereogenic centered C10-C18 fragment of iriomoteolide-3a has been accomplished. Key steps include Sharpless asymmetric dihydroxylation and epoxidation for generation of the desired stereocenters.

  DOI：

  10.1055/s-0032-1318141
• 作为产物：
  描述：

  3-(tert-butyldiphenylsilyloxy)-1-propanal 在 甲基磺酰胺 、 AD-mix-α 、 三乙胺 、 lithium hexamethyldisilazane 、 叔丁醇 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 43.0h， 生成 (3R,5S)-5-[(S)-2,2,3,3,10,10-hexamethyl-9,9-diphenyl-4,8-dioxa-3,9-disilaundecan-5-yl]-3-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Stereoselective Synthesis of the C10-C18 Fragment of Iriomoteolide-3a

  摘要：

  An efficient synthesis of the highly stereogenic centered C10-C18 fragment of iriomoteolide-3a has been accomplished. Key steps include Sharpless asymmetric dihydroxylation and epoxidation for generation of the desired stereocenters.

  DOI：

  10.1055/s-0032-1318141

文献信息

• Total Synthesis of (+)- and (−)-Sundiversifolide via Intramolecular Acylation and Determination of the Absolute Configuration
  作者：Keiko Ohtsuki、Kazumasa Matsuo、Takashi Yoshikawa、Chihiro Moriya、Kaori Tomita-Yokotani、Kozo Shishido、Mitsuru Shindo

  DOI：10.1021/ol8001333

  日期：2008.3.1

  Intramolecular acylation of an organolithium leads to an efficient stereocontrolled total synthesis of both enantiomers of sundiversifolide. The absolute configuration was determined by HPLC analysis and allelopathy assay. The gamma-lactone moiety resulted from a butenolide was obtained by the condensation of a bicyclic alpha-hydroxyhemiacetal with Ph3P=CMe(CO2R).

  有机锂的分子内酰化导致sundiversifolide的两个对映异构体的有效立体控制的全合成。通过HPLC分析和化感作用测定法确定绝对构型。通过将双环α-羟基半缩醛与Ph3P = CMe（CO2R）缩合获得由丁烯内酯产生的gamma-lactone部分。
• Total synthesis of xanthanolides
  作者：Kazumasa Matsuo、Keiko Ohtsuki、Takashi Yoshikawa、Kozo Shishido、Kaori Yokotani-Tomita、Mitsuru Shindo

  DOI：10.1016/j.tet.2010.08.061

  日期：2010.10

  The total synthesis and determination of the absolute configuration of (+)- and (-)-sundiversifolide have been achieved via intramolecular acylation and Wittig-lactonization as the key steps. The xanthanolide sesquiterpene lactones, 8-epi-xanthatin (1), dihydroxanthatin (2), and xanthatin (3) were also prepared, starting from a common intermediate derived from the synthesis of sundiversifolide. (C) 2010 Elsevier Ltd. All rights reserved.