(2S)-3-tert-butyldimethylsilyloxy-2-(4-methoxybenzyloxy)propanal | 180153-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-3-tert-butyldimethylsilyloxy-2-(4-methoxybenzyloxy)propanal
• 英文别名: (2S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(4-methoxyphenyl)methoxy]propanal
• CAS: 180153-95-1
• 化学式: C₁₇H₂₈O₄Si
• 分子量: 324.492
• InChiKey: AWZPCGFWNPFUHV-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-3-tert-butyldimethylsilyloxy-2-(4-methoxybenzyloxy)propanal 在 (S,S)-1,2-diamino-1,2-diphenylethane bis(N,N-toluenesulfonamide) 、 2,6-二叔丁基-4-甲基吡啶 、 magnesium bromide ethyl etherate 作用下， 以 二氯甲烷 为溶剂， 反应 33.08h， 生成 (1R,2R)-1-(methoxymethoxy)-1-phenyl-4-[(2S,3S)-1-[(tert-butyldimethylsilyl)oxy]-2-(4-methoxybenzyloxy)-3-methoxy]butyl-4-penten-2-ol
  参考文献：
  名称：

  用于合成复杂多元醇的 1,5-syn 和 1,5-反立体控制的双向 SE' 策略

  摘要：

  研究报告了一种双向 S E ' 策略，适用于非外消旋 1,5- syn和 1,5- anti二醇及其衍生物的立体控制合成。非外消旋 1,3,2-二氮杂硼烷助剂通过化学选择性锡-硼交换加入，以提供反应性烯丙基硼烷。收敛途径利用与两种醛的顺序反应，分别从循环、闭合和开放过渡态偏好产生立体化学结果。peloruside A片段16的合成分四步完成，由容易获得的醛9和13 组成。

  DOI：

  10.1021/ol3015682
• 作为产物：
  描述：

  叔丁基二甲基甲硅烷基缩水甘油醚 在 草酰氯 、 (S,S)-(salen)cobalt(III)(OAc) 、 三氟甲磺酸 、 水 、 二异丁基氢化铝 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 Petroleum ether 为溶剂， 反应 26.5h， 生成 (2S)-3-tert-butyldimethylsilyloxy-2-(4-methoxybenzyloxy)propanal
  参考文献：
  名称：

  Synthesis of the C21–C28 segment of pectenotoxin-4

  摘要：

  The synthesis of the C21-C28 segment of pectenotoxin-4 as the C21 Weinreb amide is described. Feasibility studies for the union of a related Weinreb amide and a functionalized alkyne are also reported. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.148

文献信息

• Antibodies with Broad Specificity to Azaspiracids by Use of Synthetic Haptens
  作者：Craig J. Forsyth、Jianyan Xu、Son T. Nguyen、Ingunn A. Samdal、Lyn R. Briggs、Thomas Rundberget、Morten Sandvik、Christopher O. Miles

  DOI：10.1021/ja066971h

  日期：2006.11.1

  The development of general, sensitive, portable, and quantitative assays for the azaspiracid (AZA) class of marine toxins is urgently needed. Use of a synthetic hapten containing rings F-I of AZA to generate antibodies that cross-react with the AZAs via their common C28-C40 domain and use of these antibodies in ELISA and immunoaffinity columns are reported. This approach has many advantages over using intact azaspiracids (AZAs) derived from environmental samples or total synthesis as haptens for antibody development. A derivative of the levorotatory C28-C40 azaspiracid domain (1) was synthesized efficiently using a one-pot Staudinger reduction/intramolecular aza-Wittig reaction-imine capture sequence to form the H-I ring spiroaminal and a double intramolecluar hetero-Michael addition to assemble the F-G ring ketal. Conjugation of the hapten 1 to cBSA and immunization in sheep generated antibodies that recognized and bound to ovalbumin-conjugated 1 in the absence of AZA1. This binding was inhibited by 1 in a concentration-dependent manner. A mixture of AZA1, AZA2, AZA3, and AZA6 caused a degree of inhibition of antibody binding consistent with its total AZA content, rather than just its content of AZA1. This result suggests that the antibodies also have a similar affinity for AZA2, AZA3, and AZA6 as they do for AZA1 and that such antibodies are suitable for analysis of AZAs in shellfish samples.
• A Bidirectional S_E′ Strategy for 1,5-<i>syn</i> and 1,5-<i>anti</i> Stereocontrol toward the Synthesis of Complex Polyols
  作者：David R. Williams、Christopher D. Claeboe、Bo Liang、Nicolas Zorn、Nicholas S. C. Chow

  DOI：10.1021/ol3015682

  日期：2012.8.3

  Studies report a bidirectional SE′ strategy applicable for the stereocontrolled synthesis of nonracemic 1,5-syn and 1,5-anti diols and their derivatives. Nonracemic 1,3,2-diazaborolidine auxiliaries are incorporated by chemoselective tin–boron exchange to provide reactive allylic boranes. The convergent pathway utilizes sequential reactions with two aldehydes producing stereochemical outcomes from

  研究报告了一种双向 S E ' 策略，适用于非外消旋 1,5- syn和 1,5- anti二醇及其衍生物的立体控制合成。非外消旋 1,3,2-二氮杂硼烷助剂通过化学选择性锡-硼交换加入，以提供反应性烯丙基硼烷。收敛途径利用与两种醛的顺序反应，分别从循环、闭合和开放过渡态偏好产生立体化学结果。peloruside A片段16的合成分四步完成，由容易获得的醛9和13 组成。
• Synthesis of the C21–C28 segment of pectenotoxin-4
  作者：Robert V. Kolakowski、Lawrence J. Williams

  DOI：10.1016/j.tetlet.2007.04.148

  日期：2007.7

  The synthesis of the C21-C28 segment of pectenotoxin-4 as the C21 Weinreb amide is described. Feasibility studies for the union of a related Weinreb amide and a functionalized alkyne are also reported. (c) 2007 Elsevier Ltd. All rights reserved.