3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-5-en-1-al | 910330-83-5

• 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: 3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-5-en-1-al
• 英文别名: (3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-4-methylhex-5-enal
• CAS: 910330-83-5
• 化学式: C₁₃H₂₆O₂Si
• 分子量: 242.434
• InChiKey: KULUFLSKKBSAMO-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-5-en-1-al 、 2-[(2R,6S)-6-(2-oxopropyl)oxan-2-yl]ethyl 2,2-dimethylpropanoate 在 三甲基氯硅烷 、 lithium diisopropyl amide 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以24%的产率得到
  参考文献：
  名称：

  Synthesis of the C1–C16 fragment of spirastrellolide A

  摘要：

  Synthesis of the Cl-C16 fragment of spirastrellolide A is described here featuring Sharpless asymmetric epoxidation, an acid promoted O-1,4-addition, and Mukaiyama 1,3-anti-aldol. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.067
• 作为产物：
  描述：

  3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-5-en-1-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以91%的产率得到3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-5-en-1-al
  参考文献：
  名称：

  Toward the Synthesis of Spirastrellolide B:  A Synthesis of the C1−C23 Subunit

  摘要：

  A synthesis of the C1-C23 subunit of spirastrellolide B is described. The synthesis features two applications of a Kulinkovich-cyclopropanol ring-opening strategy for the coupling of esters with olefins to produce ketones.

  DOI：

  10.1021/ol702955m

文献信息

• Total Synthesis of 8-Deshydroxyajudazol B
  作者：Stephen Birkett、Danny Ganame、Bill C. Hawkins、Sébastien Meiries、Tim Quach、Mark A. Rizzacasa

  DOI：10.1021/ol200331u

  日期：2011.4.15

  The total synthesis of a stereoisomer of 8-deshydroxyajudazol B (4), the putative biosynthetic intermediate of the ajudazols A (1) and B (2), is described. The key steps in the synthesis included an intramolecular Diels−Alder (IMDA) reaction to secure the isochromanone fragment, a novel selective acylation/O,N-shift to give a hydroxyamide which was cyclized to the oxazole and a high yielding Sonogashira

  描述了8-去羟基ajudazol B（4）的立体异构体的全合成，这是阿杜唑A（1）和B（2）的假定生物合成中间体。合成的关键步骤包括分子内Diels-Alder（IMDA）反应以确保异苯并二氢吡喃酮片段的发生，新型的选择性酰化/ O，N移位以生成羟酰胺，然后将其环化成恶唑，以及高产率的Sonogashira偶联形成C18-C19键。然后，部分炔烃还原得到目标4。
• ASSEMBLY OF THE SOUTHERN MACROCYCLIC HALF OF (+)-SPIRASTRELLOLIDE A THROUGH CYCLIC ACETAL TETHERED RING-CLOSING METATHESIS AND 1,3-ANTI-MUKAIYAMA-ALDOL
  作者：Richard P. Hsung、Yu Tang、Jin-Haek Yang、Jia Liu、Chao-Chao Wang、Ming-Can Lv、Yi-Biao Wu、Xue-Liang Yu、Changhong Ko

  DOI：10.3987/com-12-s(n)54

  日期：——

  We describe herein details of our efforts in syntheses of A-ring and BC-ring of (+)-spirastrellolide A. While the former would constitute a facile 12-step synthetic endeavor starting from 1,5-pentanediol, the latter would showcase a cyclic acetal-tethered ring-closing metathesis [RCM] method that was developed in our lab for de novo synthesis of spiroketals. Constructing the entire Southern Half of the macrocycle would require 1,3-anti-Mukaiyama aldol addition for connecting A-ring and BC-ring specifically at C10 and C11, thereby culminating a 17-step approach for the Southern Macrocyclic Half linearly from (+)-2,3-(O)-iso-propylidene-L-threitol. Also discussed here is the possibility of pursuing a more convergent approach toward the assembly of the Southern Half through first connecting A-ring and C-ring via acetal formation that would first link together the free C13-OH with C17 at the spiro-BC-ring junction. An ensuing application of our cyclic acetal-tethered RCM strategy to close B-ring would adopt this cyclic acetal intermediate.
• Synthesis of the C1–C16 fragment of spirastrellolide A
  作者：Jia Liu、Jin Haek Yang、Changhong Ko、Richard P. Hsung

  DOI：10.1016/j.tetlet.2006.06.067

  日期：2006.8

  Synthesis of the Cl-C16 fragment of spirastrellolide A is described here featuring Sharpless asymmetric epoxidation, an acid promoted O-1,4-addition, and Mukaiyama 1,3-anti-aldol. (c) 2006 Elsevier Ltd. All rights reserved.
• Toward the Synthesis of Spirastrellolide B:  A Synthesis of the C1−C23 Subunit
  作者：Katie A. Keaton、Andrew J. Phillips

  DOI：10.1021/ol702955m

  日期：2008.3.1

  A synthesis of the C1-C23 subunit of spirastrellolide B is described. The synthesis features two applications of a Kulinkovich-cyclopropanol ring-opening strategy for the coupling of esters with olefins to produce ketones.