(3S,4S)-4-tert-butyldiphenylsilyloxy-3-methyl-pentan-1-al | 945903-61-7

• 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: (3S,4S)-4-tert-butyldiphenylsilyloxy-3-methyl-pentan-1-al
• 英文别名: (3S,4S)-4-((tert-butyldiphenylsilyl)oxy)-3-methylpentanal；(3S,4S)-4-[tert-butyl(diphenyl)silyl]oxy-3-methylpentanal
• CAS: 945903-61-7
• 化学式: C₂₂H₃₀O₂Si
• 分子量: 354.565
• InChiKey: FZYRGPBXYWBYFS-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  (3S,4S)-4-tert-butyldiphenylsilyloxy-3-methyl-pentan-1-al 在 四丁基碘化铵 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 29.0h， 生成 (5R,7S,8S)-5-((S)-but-3-en-2-yl)-7,8,11,11-tetramethyl-10,10-diphenyl-2,4,9-trioxa-10-siladodecane
  参考文献：
  名称：

  大环内酯异丁烯内酯-1b结构的对映选择性全合成

  摘要：

  通过收敛方案实现了大环内酯iriomoteolide-1b拟议结构的对映选择性全合成，其特征在于烯的对映选择性有机催化转移氢化，即Julia-Kocienski烯烃化反应，建立了C15-C16 E-烯烃部分，与环丙基-烯丙基重排有关的Kulinkovich反应产生烯丙基锡烷和三氟甲磺酸and，羧酸促进烯丙基锡烷和醛在α-位与叔醇之间的烯丙基化。大环内酯2的构建是通过在室温下成功地利用5摩尔％Grubbs的第二代催化剂和E-异构体作为单一产品成功实施RCM来实现的。

  DOI：

  10.1016/j.tet.2011.06.025
• 作为产物：
  描述：

  (2S,3S)-3-甲基-4-戊烯-2-醇 在 咪唑 、 重铬酸吡啶 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 (3S,4S)-4-tert-butyldiphenylsilyloxy-3-methyl-pentan-1-al
  参考文献：
  名称：

  Towards the biosynthesis of the aromatic products of the Mediterranean mollusc Scaphander lignarius: isolation and synthesis of analogues of lignarenones

  摘要：

  Secondary metabolites of the Mediterranean mollusc Scaphander lignarius from different collection sites have been investigated, proving the constant presence of a number of minor metabolites correlated to the already known lignarenones. Complete characterization of the new metabolites has been supported by enantioselective synthesis. The data are consistent with the origin of this unique class of omega-phenyloctanoids from a common polyketide pathway. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.061

文献信息

• Synthesis of the macrocyclic core of iriomoteolide-1a
  作者：Shuo Li、Zheng Chen、Zhengshuang Xu、Tao Ye

  DOI：10.1039/c0cc00915f

  日期：——

  The fully functionalized macrocyclic core of the marine natural product iriomoteolide-1a has been successfully constructed in a convergent and enantioselective manner.

  海洋天然产物iriomoteolide-1a的完全功能化的大环核心已经成功以聚合和选择性对映体的方式构建。
• Synthesis of C13-C23 Fragment of Iriomoteolide-1a
  作者：Teck-Peng Loh、Shun-Yi Wang、Yen-Jin Chin

  DOI：10.1055/s-0029-1218152

  日期：2009.11

  Highly efficient asymmetric conjugate addition of MeMgBr to α,β-unsaturated esters catalyzed by CuI/Tol-BINAP, Paterson aldol, organocatalytic aldol, and cross-metathesis reactions were applied in the synthesis of C13-C23 fragment of Iriomoteolide-1a. asymmetric conjugate addition - organocatalytic aldol - cross-metathesis - Iriomoteolide-1a

  将MeMgBr高效不对称共轭加成到CuI / Tol-BINAP，Paterson醛醇，有机催化醛醇和交叉复分解反应催化的α，β-不饱和酯中，合成Iriomoteolide-1a的C13-C23片段。 不对称共轭加成-有机催化羟醛-交叉复分解-Iriomoteolide-1a
• Synthetic Studies towards Iriomoteolide-1a: Construction of the C13-C23 Fragment
  作者：Gang Zhao、Zhengqing Ye、Lisheng Deng、Shan Qian

  DOI：10.1055/s-0029-1217728

  日期：2009.9

  A stereoselective synthesis of the C13-C23 segment of iriomoteolide-1a was achieved using, as key steps, a highly stereocontrolled crotylation to build the stereocenters at C18 and C19 and a Julia-Kocienski olefination to establish the C15-C16 E-olefin moiety.

  通过采用高度立体控制的克罗提化反应建立C18和C19的立体中心，以及朱莉亚-科琴斯基烯化反应形成C15-C16 E-烯烃部分，成功实现了Iriomoteolide-1a的C13-C23片段的立体选择性合成。
• Towards the biosynthesis of the aromatic products of the Mediterranean mollusc Scaphander lignarius: isolation and synthesis of analogues of lignarenones
  作者：Giorgio Della Sala、Adele Cutignano、Angelo Fontana、Aldo Spinella、Gianpiero Calabrese、Anna Domenech Coll、Giuliana d'Ippolito、Carmela Della Monica、Guido Cimino

  DOI：10.1016/j.tet.2007.04.061

  日期：2007.7

  Secondary metabolites of the Mediterranean mollusc Scaphander lignarius from different collection sites have been investigated, proving the constant presence of a number of minor metabolites correlated to the already known lignarenones. Complete characterization of the new metabolites has been supported by enantioselective synthesis. The data are consistent with the origin of this unique class of omega-phenyloctanoids from a common polyketide pathway. (C) 2007 Elsevier Ltd. All rights reserved.
• Enantioselective total synthesis of the proposed structure of macrolide iriomoteolide-1b
  作者：Zhengqing Ye、Tingyi Gao、Gang Zhao

  DOI：10.1016/j.tet.2011.06.025

  日期：2011.8

  an enantioselective organocatalytic transfer hydrogenation of enal, a Julia–Kocienski olefination to establish the C15–C16 E-olefin moiety, a Kulinkovich reaction associated with cyclopropyl-allyl rearrangement to produce allyl stannane and ytterbium triflate and carboxylic acid promoted allylation between allyl stannane and aldehyde with tertiary alcohol at the α-position. The construction of macrolide

  通过收敛方案实现了大环内酯iriomoteolide-1b拟议结构的对映选择性全合成，其特征在于烯的对映选择性有机催化转移氢化，即Julia-Kocienski烯烃化反应，建立了C15-C16 E-烯烃部分，与环丙基-烯丙基重排有关的Kulinkovich反应产生烯丙基锡烷和三氟甲磺酸and，羧酸促进烯丙基锡烷和醛在α-位与叔醇之间的烯丙基化。大环内酯2的构建是通过在室温下成功地利用5摩尔％Grubbs的第二代催化剂和E-异构体作为单一产品成功实施RCM来实现的。