(R)-1-((tert-butyldiphenylsilyl)oxy)pent-4-en-2-yl acrylate | 445289-97-4

• 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: (R)-1-((tert-butyldiphenylsilyl)oxy)pent-4-en-2-yl acrylate
• 英文别名: (R)-1-(tert-butyldiphenylsilyloxy)pent-4-en-2-yl acrylate；[(2R)-1-[tert-butyl(diphenyl)silyl]oxypent-4-en-2-yl] prop-2-enoate
• CAS: 445289-97-4
• 化学式: C₂₄H₃₀O₃Si
• 分子量: 394.586
• InChiKey: ZOHZQPIHZVAVKF-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (R)-1-((tert-butyldiphenylsilyl)oxy)pent-4-en-2-yl acrylate 在 Grubbs catalyst first generation 、 草酰氯 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 36.33h， 生成 (R)-6-formyl-2-isopropyloxy-5,6-dihydro-2H-pyran
  参考文献：
  名称：

  Coibacins A and B: Total Synthesis and Stereochemical Revision

  摘要：

  The interface between synthetic organic chemistry and natural products was explored in order to unravel the structure of coibacin A, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp. that exhibits selective antileishmanial activity and potent anti-inflammatory properties. Our synthetic plan focused on a convergent strategy that allows rapid access to the desired target by coupling of three key fragments involving E-selective Wittig and modified Julia olefinations. CD measurements and comparative HPLC analyses of the natural product and four synthetic stereoisomers led to determination of its absolute configuration, thus correcting the original assignment at C-5 and unambiguously establishing those at C-16 and C-18. Additionally, we synthesized coibacin B on the basis of the assignment of configuration for coibacin A.

  DOI：

  10.1021/jo402339y
• 作为产物：
  描述：

  (R)-(tert-butyldiphenylsilyloxy)methyloxirane 在 TEA 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (R)-1-((tert-butyldiphenylsilyl)oxy)pent-4-en-2-yl acrylate
  参考文献：
  名称：

  Total synthesis of (R)-(+)-goniothalamin and (R)-(+)-goniothalamin oxide: first application of the sulfoxide-modified Julia olefination in total synthesis

  摘要：

  A short and efficient synthesis of (R)-(+)-goniothalamin 1 and (R)-(+)-goniothalamin oxide 2 is described. During this approach, the sulfoxide-modified Julia olefination was used as a key step to connect aldehyde 5 to sulfoxide 6. The desired styryl-containing adduct is obtained in good yield and with excellent E/Z selectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.054

文献信息

• Stereoselective synthesis of the C1–C12 subunit of (−)-callystatin A
  作者：Sadagopan Raghavan、Sheelamanthula Rajendar

  DOI：10.1016/j.tetlet.2015.05.089

  日期：2015.7

  A stereoselective synthesis of the C1-C12 fragment of callystatin A is disclosed. The two stereocenters at C5 and C10 were created by an organocatalytic reaction and a diastereoselective alkylation, respectively. The trisubstituted double bond was introduced by a hydroxy directed hydrostannylation followed by the Negishi reaction. The lactone ring resulted from a ring-closing metathesis reaction. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of (R)-(−)-argentilactone
  作者：Trond Vidar Hansen

  DOI：10.1016/s0957-4166(02)00138-6

  日期：2002.4

  A synthesis of (R)-(-)-argentilactone is reported starting from the (S)-enantiomer of glycidol. The synthesis is based on ring closing metathesis of the acrylic ester of (R)-1-O-(tert-butyldiphenylsilyl)-4-penten-1,2-diol 4. (C) 2002 Elsevier Science Ltd. All rights reserved.
• An efficient synthesis of synargentolide A from d-mannitol
  作者：Ahmed Kamal、Moku Balakrishna、Papagari Venkat Reddy、Shaikh Faazil

  DOI：10.1016/j.tetasy.2010.10.001

  日期：2010.10

  An efficient synthesis of synargentolide A is described by using D-mannitol and D-malic acid The key features of the synthetic strategy include Wittig olefination ring closing-metathesis reaction and cross-metathesis reaction for the formation of synargentolide A (C) 2010 Elsevier Ltd All rights reserved
• Coibacins A and B: Total Synthesis and Stereochemical Revision
  作者：Vânia M. T. Carneiro、Carolina M. Avila、Marcy J. Balunas、William H. Gerwick、Ronaldo A. Pilli

  DOI：10.1021/jo402339y

  日期：2014.1.17

  The interface between synthetic organic chemistry and natural products was explored in order to unravel the structure of coibacin A, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp. that exhibits selective antileishmanial activity and potent anti-inflammatory properties. Our synthetic plan focused on a convergent strategy that allows rapid access to the desired target by coupling of three key fragments involving E-selective Wittig and modified Julia olefinations. CD measurements and comparative HPLC analyses of the natural product and four synthetic stereoisomers led to determination of its absolute configuration, thus correcting the original assignment at C-5 and unambiguously establishing those at C-16 and C-18. Additionally, we synthesized coibacin B on the basis of the assignment of configuration for coibacin A.
• Total synthesis of (R)-(+)-goniothalamin and (R)-(+)-goniothalamin oxide: first application of the sulfoxide-modified Julia olefination in total synthesis
  作者：Jiří Pospíšil、István E. Markó

  DOI：10.1016/j.tetlet.2006.06.054

  日期：2006.8

  A short and efficient synthesis of (R)-(+)-goniothalamin 1 and (R)-(+)-goniothalamin oxide 2 is described. During this approach, the sulfoxide-modified Julia olefination was used as a key step to connect aldehyde 5 to sulfoxide 6. The desired styryl-containing adduct is obtained in good yield and with excellent E/Z selectivity. (c) 2006 Elsevier Ltd. All rights reserved.