(2R)-2-(tert-butyldimethylsiloxymethyl)butanal | 161449-33-8

• 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: (2R)-2-(tert-butyldimethylsiloxymethyl)butanal
• 英文别名: (R)-2-((tert-butyldimethylsilyloxy)methyl)butanal；(2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]butanal
• CAS: 161449-33-8
• 化学式: C₁₁H₂₄O₂Si
• 分子量: 216.396
• InChiKey: KBUBYOCURNFBFA-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (2R)-2-(tert-butyldimethylsiloxymethyl)butanal 在 4-二甲氨基吡啶 、 ruthenium(II) bis(triphenylphosphine) dichloride 、 二叔丁基过氧化物 、 4 A molecular sieve 、 四丁基氟化铵 、 三乙胺 、 lithium chloride 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 53.58h， 生成 (3S)-2-(N-benzylideneamino)-3-(chloromethyl)valeronitrile
  参考文献：
  名称：

  Gaucher, Anne; Ollivier, Jean; Marguerite, Jacqueline, Canadian Journal of Chemistry, 1994, vol. 72, # 5, p. 1312 - 1327

  摘要：

  DOI：
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 、 草酰氯 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.33h， 生成 (2R)-2-(tert-butyldimethylsiloxymethyl)butanal
  参考文献：
  名称：

  Gaucher, Anne; Ollivier, Jean; Marguerite, Jacqueline, Canadian Journal of Chemistry, 1994, vol. 72, # 5, p. 1312 - 1327

  摘要：

  DOI：

文献信息

• New General Method for Regio- and Stereoselective Allylic Substitution with Aryl and Alkenyl Coppers Derived from Grignard Reagents
  作者：Yohei Kiyotsuka、Yuji Katayama、Hukum P. Acharya、Tomonori Hyodo、Yuichi Kobayashi

  DOI：10.1021/jo802426g

  日期：2009.3.6

  Allylic substitution with sp2-carbon reagents (aryl and alkenyl anions) was realized by using allylic picolinates and copper reagents derived from RMgBr and CuBr·Me2S to afford anti SN2′ products regio- and stereoselectively. Steric and electronic factors in the reagents and the size of the methylene substituents around the allylic moiety marginally affected the selectivity. The reaction system was

  通过使用烯丙基吡啶甲酸酯和衍生自RMgBr和CuBr·Me 2 S的铜试剂实现Sp 2-碳试剂（芳基和烯基阴离子）的烯丙基取代，可以在区域和立体选择性地提供抗S N 2'产物。试剂中的立体和电子因素以及烯丙基部分周围的亚甲基取代基的大小在一定程度上影响了选择性。该反应系统也与烷基试剂相容。此外，该取代被应用于四元中心的构建和（-）-倍半茶烯酚的合成。吸电子的C的吡啶基的性质和螯合（═ ö）-C 5 H ^ 4 Ñ到MgBr 2 发现原位产生的碳负责替代的高效率。
• Synthesis and Antibacterial Activity of Four Stereoisomers of the Spider-Pathogenic Fungus Metabolite Torrubiellone D
  作者：Sebastian Bruckner、Ursula Bilitewski、Rainer Schobert

  DOI：10.1021/acs.orglett.6b00245

  日期：2016.3.4

  Four stereoisomers of the spider-pathogenic fungus metabolite torrubiellone D were synthesized for the first time in 10% overall yield starting from l-tyrosine or d-tyrosine. The 3-decatrienoyl side chain was assembled and attached via (E)-selective HWE and Wittig olefinations. Their antibiotic activities against drug-susceptible Escherichia coli strains differed considerably.

  蜘蛛致病性真菌代谢产物托瑞比隆D的四种立体异构体以1-酪氨酸或d-酪氨酸为起始原料，首次以10％的总收率合成。3-癸三烯酰基侧链通过（E）-选择性HWE和Wittig烯化反应组装并连接。它们对药物敏感的大肠杆菌菌株的抗生素活性差异很大。
• Total syntheses of (+)-spiculoic acid A and (+)-zyggomphic acid, new marine natural products of polyketide origin
  作者：Daisuke Matsumura、Toshimasa Takarabe、Takumi Toda、Takashi Hayamizu、Kiyoto Sawamura、Ken-ichi Takao、Kin-ichi Tadano

  DOI：10.1016/j.tet.2011.04.006

  日期：2011.9

  The total syntheses of both natural (+)-spiculoic acid A and (+)-zyggomphic acid, new cytotoxic marine natural products of polyketide origin, have been accomplished for the first time. These syntheses were achieved by the highly stereoselective and high-yielding intramolecular Diels–Alder reaction of a functionalized (E,E,E)-2,7,9-dodecanal derivative to construct the core tetrahydroindan-2-one skeleton

  天然（+）-吡啶甲酸A和（+）-zygomphmphic酸（聚酮化合物来源的新的细胞毒性海洋天然产物）的总合成已首次完成。这些合成是通过功能化的（E，E，E）-2,7,9-十二碳六烯衍生物的高度立体选择性和高产率的分子内Diels-Alder反应实现的，以构建核心的四氢茚满-2-一骨架。还合成了（+）-吡啶甲酸A的立体异构体，即（2 R，5 S，6 R）-异构体。描述了这些全部合成的细节。
• Total Synthesis of Leustroducsin B
  作者：Kazuyuki Miyashita、Tomoyuki Tsunemi、Takafumi Hosokawa、Masahiro Ikejiri、Takeshi Imanishi

  DOI：10.1021/jo8005599

  日期：2008.7.1

  Leustroducsin B was synthesized via a convergent route based on division of the leustroducsin molecule into three segments A, B, and C. Two coupling reactions (Julia coupling reaction and Nozaki-Hiyama-Kishi (NHK) reaction) were employed for coupling of segments A and 13: segment A, for the Julia coupling reaction was prepared by a combination of Sharpless asymmetric epoxidation and an epoxide-cleavage reaction with an organoaluminum reagent, while segment A, for the NHK reaction was synthesized from optically active alcohol that had previously been prepared by lipase-catalyzed kinetic resolution. Segment B, whose structure was modified with some functional groups, was synthesized from (R)-malic acid by a combination of Wittig reaction and Sharpless asymmetric dihydroxylation, and segment C, containing a cyclohexane moiety, was prepared by asymmetric Diels-Alder reaction. Segment B was first coupled with segment A, via the Julia coupling reaction, but the yield was low due to unexpected epimerization. The NHK reaction of segment A2 proceeded to give the coupling product in good yield. This product was coupled with segment C via Wittig and Stille coupling reactions, and finally, phosphorylation was carried out by partial hydrolysis of a cyclic phosphate to give leustroducsin B.
• Total synthesis of (+)-spiculoic acid A
  作者：Daisuke Matsumura、Takumi Toda、Takashi Hayamizu、Kiyoto Sawamura、Ken-ichi Takao、Kin-ichi Tadano

  DOI：10.1016/j.tetlet.2009.02.101

  日期：2009.7

  The total synthesis of natural (+)-spiculoic acid A, a new cytotoxic marine natural product of polyketide origin, has been accomplished for the first time. The key step of the total synthesis was a stereciselective and high-yielding intramolecular Diels-Alder reaction of a highly functionalized (E,E,E)-2,7,9-dodecanal derivative for the construction of the core tetrahydroindan-2-one skeleton. (C) 2009 Elsevier Ltd. All rights reserved.