2-[(2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-3-methylbut-2-enyl]oxolan-2-yl]acetaldehyde | 1279710-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2-[(2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-3-methylbut-2-enyl]oxolan-2-yl]acetaldehyde
• CAS: 1279710-22-3
• 化学式: C₁₇H₃₂O₃Si
• 分子量: 312.525
• InChiKey: FXGSZCCYZSVUBZ-BZUAXINKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-3-methylbut-2-enyl]oxolan-2-yl]acetaldehyde 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 (-)-diisopinocamphenylborane chloride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of the C22–C37 segment of prorocentin

  摘要：

  The synthesis of the C22-C37 segment of prorocentin, isolated from the dinoflagellate Prorocentrum lima, was achieved. Because the relative stereochemical relationship between C26 and other stereocenters (C28/C31/C32 established as R*/R*/R*) in the C22-C37 region of natural prorocentin has not yet been determined, both epimers at C26 of the C22-C37 segment were selectively constructed. The synthesis was based on a 5-exo epoxide ring opening reaction to form an oxolane (E-ring). Brown asymmetric methallylation to install the C26-stereocenter, acryloylation of the resulting alcohol, and ring-closing olefin metathesis to establish the Z-olefin at C23/C24. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.042
• 作为产物：
  描述：

  (R)-10-(2-((4-methoxybenzyl)oxy)ethyl)-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradec-6-yne 在 吡啶 、 2,6-二甲基吡啶 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 正丁基锂 、 草酰氯 、 D-(-)-酒石酸二乙酯 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 氢气 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 二甲基亚砜 、 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 、 苯 为溶剂， 生成 2-[(2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-3-methylbut-2-enyl]oxolan-2-yl]acetaldehyde
  参考文献：
  名称：

  Synthesis of the C22–C37 segment of prorocentin

  摘要：

  The synthesis of the C22-C37 segment of prorocentin, isolated from the dinoflagellate Prorocentrum lima, was achieved. Because the relative stereochemical relationship between C26 and other stereocenters (C28/C31/C32 established as R*/R*/R*) in the C22-C37 region of natural prorocentin has not yet been determined, both epimers at C26 of the C22-C37 segment were selectively constructed. The synthesis was based on a 5-exo epoxide ring opening reaction to form an oxolane (E-ring). Brown asymmetric methallylation to install the C26-stereocenter, acryloylation of the resulting alcohol, and ring-closing olefin metathesis to establish the Z-olefin at C23/C24. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.042

文献信息

• Synthesis of the C22–C37 segment of prorocentin
  作者：Atsushi Takemura、Yasushi Katagiri、Kenshu Fujiwara、Hidetoshi Kawai、Takanori Suzuki

  DOI：10.1016/j.tetlet.2011.01.042

  日期：2011.3

  The synthesis of the C22-C37 segment of prorocentin, isolated from the dinoflagellate Prorocentrum lima, was achieved. Because the relative stereochemical relationship between C26 and other stereocenters (C28/C31/C32 established as R*/R*/R*) in the C22-C37 region of natural prorocentin has not yet been determined, both epimers at C26 of the C22-C37 segment were selectively constructed. The synthesis was based on a 5-exo epoxide ring opening reaction to form an oxolane (E-ring). Brown asymmetric methallylation to install the C26-stereocenter, acryloylation of the resulting alcohol, and ring-closing olefin metathesis to establish the Z-olefin at C23/C24. (C) 2011 Elsevier Ltd. All rights reserved.