ethyl 2-((2R,3S,6R)-6-((6S,1E)-6-(tert-butyldimethylsilyloxy)hept-1-enyl)-3-hydroxytetrahydro-2H-pyran-2-yl)acetate | 1292793-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: ethyl 2-((2R,3S,6R)-6-((6S,1E)-6-(tert-butyldimethylsilyloxy)hept-1-enyl)-3-hydroxytetrahydro-2H-pyran-2-yl)acetate
• 英文别名: ethyl 2-[(2R,3S,6R)-6-[(E,6S)-6-[tert-butyl(dimethyl)silyl]oxyhept-1-enyl]-3-hydroxyoxan-2-yl]acetate
• CAS: 1292793-66-8
• 化学式: C₂₂H₄₂O₅Si
• 分子量: 414.658
• InChiKey: SMXXUMYOXUNIHJ-KXIWMRAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2E)-ethyl 3-((3R,9S,4E)-(9-tert-butyldimethylsilyloxy)-1-(1,3-dithian-2-yl)dec-4-en-3-yloxy)acrylate 在 samarium diiodide 、 碳酸氢钠 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 48.67h， 生成 ethyl 2-((2R,3S,6R)-6-((6S,1E)-6-(tert-butyldimethylsilyloxy)hept-1-enyl)-3-hydroxytetrahydro-2H-pyran-2-yl)acetate 、 ethyl 2-((2S,3R,6R)-6-((6S,1E)-6-(tert-butyldimethylsilyloxy)hept-1-enyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-acetate
  参考文献：
  名称：

  Formal total synthesis of aspergillide A

  摘要：

  The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C-4-C-14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into beta-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.016

文献信息

• Formal total synthesis of aspergillide A
  作者：Yuko Izuchi、Nobuhiro Kanomata、Hiroyuki Koshino、Yayoi Hongo、Tadashi Nakata、Shunya Takahashi

  DOI：10.1016/j.tetasy.2011.01.016

  日期：2011.1

  The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C-4-C-14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into beta-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1. (C) 2011 Elsevier Ltd. All rights reserved.