1-(tert-butyldimethylsilyloxy)-2,4-dimethylhex-5-en-3-ol | 152377-58-7

• 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: 1-(tert-butyldimethylsilyloxy)-2,4-dimethylhex-5-en-3-ol
• 英文别名: 1-(tert-butyldimethylsiloxy)-2,4-dimethyl-hex-5-en-3-ol；(2R,3S,4R)-1-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethylhex-5-en-3-ol
• CAS: 152377-58-7
• 化学式: C₁₄H₃₀O₂Si
• 分子量: 258.476
• InChiKey: JKEWULNLXLQSQZ-UPJWGTAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(tert-butyldimethylsilyloxy)-2,4-dimethylhex-5-en-3-ol 在 swern reagent 、 bis(triphenylphosphine)palladium(0) 、 2,3-二巯基丁二酸 、 sodium hexamethyldisilazane 、 sodium hydride 、 臭氧 、 三氟乙酸 作用下， 生成 (Z)-(4S,5R,6R)-5-(4-Methoxy-benzyloxy)-4,6-dimethyl-deca-7,9-dien-3-one
  参考文献：
  名称：

  Nerenberg; Hung; Somers, Journal of the American Chemical Society, 1993, vol. 115, # 26, p. 12621 - 12622

  摘要：

  DOI：
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-(tert-butyldimethylsilyloxy)-2,4-dimethylhex-5-en-3-ol
  参考文献：
  名称：

  聚醚离子载体抗生素罗替诺星的生物活性与绝对立体化学无关

  摘要：

  使用收敛合成来获得聚醚抗生素鲁替诺星的两种对映体和非对映体变体，以探究改变自然构型立体化学的生物学后果。针对广泛的细菌和哺乳动物细胞测试这些化合物揭示了所有测试细胞中绝对立体化学的独立性。

  DOI：

  10.1002/cbic.202400013

文献信息

• Eight-Step Synthesis of Routiennocin
  作者：Kenji Matsumoto、Sergey A. Kozmin

  DOI：10.1002/adsc.200700537

  日期：2008.3.7

  Routiennocin is a member of a family of polycyclic pyrrole ether antibiotics that simultaneously uncouple oxidative phosphorylation and inhibit ATPase as a result of selective complexation of divalent metal ions. We describe a concise synthesis of routiennocin with the longest linear sequence of 8 steps. Our synthesis features a unique bi-directional strategy, which entails a sequential ring-opening/cross

  Routiennocin是多环吡咯醚抗生素家族的成员，该抗生素同时由于二价金属离子的选择性络合而解偶联氧化磷酸化并抑制ATPase。我们描述了具有8个步骤的最长线性序列的鲁替诺霉素的简明合成。我们的合成具有独特的双向策略，需要高度应变的环丙烯酮缩醛连续开环/交叉复分解。这种方法能够使这种天然产物的完全延伸的聚酮亚基由容易获得的均丙醇前体快速且高度收敛地组装。
• Diastereoselective Chain-Elongation Reactions Using Microreactors for Applications in Complex Molecule Assembly
  作者：Catherine F. Carter、Heiko Lange、Daiki Sakai、Ian R. Baxendale、Steven V. Ley

  DOI：10.1002/chem.201003148

  日期：2011.3.14

  Diastereoselective chain‐elongation reactions are important transformations for the assembly of complex molecular structures, such as those present in polyketide natural products. Here we report new methods for performing crotylation reactions and homopropargylation reactions by using newly developed low‐temperature flow‐chemistry technology. In‐line purification protocols are described, as well as

  非对映选择性链延长反应是组装复杂分子结构（例如存在于聚酮化合物天然产物中的那些）的重要转变。在这里，我们报告了通过使用最新开发的低温流化学技术进行丁烯二酰化反应和均丙基化反应的新方法。描述了在线纯化规程，以及crotylation规程在自动化多步骤序列中的应用。
• A More Comprehensive and Highly Practical Solution to Enantioselective Aldehyde Crotylation
  作者：Hyunwoo Kim、Stephen Ho、James L. Leighton

  DOI：10.1021/ja200712f

  日期：2011.5.4

  The enantioselective crotylation of aldehydes with 1,2-diaminochlorocrotylsilane reagents is effectively catalyzed by Sc(OTf)(3). The one significant limitation on the utility of these reagents - substrate scope - has thus been addressed. The net result is the most comprehensive and highly practical method for enantioselective aldehyde crotylation yet advanced.
• A Multifaceted Phosphate Tether:  Application to the C1−C14 Subunit of Dolabelides A−D
  作者：Joshua D. Waetzig、Paul R. Hanson

  DOI：10.1021/ol7025944

  日期：2008.1.1

  A phosphate tether approach to the C1-14 subunit of dolabelide is described. The phosphate tether serves a multifaceted role mediating several processes, including (i) diastereotopic differentiation via RCM, (ii) selective CM by imparting Type III behavior to the exocyclic olefin, (iii) regioselective hydrogenation, and (iv) regioselective Pd(0)-catalyzed reductive opening of the bicyclic phosphate. Overall, this strategy uses orthogonal protecting- and leaving-group properties innate to phosphate esters to rapidly assembly the titled subunit.
• Crotylboron-Based Synthesis of the Polypropionate Units of Chaxamycins A/D, Salinisporamycin, and Rifamycin S
  作者：Ming Chen、William R. Roush

  DOI：10.1021/jo3008226

  日期：2013.1.4

  Syntheses of the C(15)-C(27) fragments of chaxamycins A/D, rifamycin S, and the C(12)-C(24) fragment of salinisporamycin have been accomplished in 10 steps from commercially available starting materials. Three crotylboron reagents were utilized to construct the seven contiguous stereocenters in these fragments with excellent stereoselectivity.