5-<(tert-Butyldiphenylsilyl)oxy>-4-methylpentanal | 165069-73-8

• 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: 5-<(tert-Butyldiphenylsilyl)oxy>-4-methylpentanal
• 英文别名: (S)-5-(tert-butyldiphenylsilyloxy)-4-methylpentanal；5-[(tert-Butyldiphenylsilyl)oxy]-4-methylpentanal；(4S)-5-[tert-butyl(diphenyl)silyl]oxy-4-methylpentanal
• CAS: 165069-73-8
• 化学式: C₂₂H₃₀O₂Si
• 分子量: 354.565
• InChiKey: HUXZBJIGWNVBOJ-IBGZPJMESA-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：
  9
• 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：

  5-<(tert-Butyldiphenylsilyl)oxy>-4-methylpentanal 在 2,6-二甲基吡啶 、 lithium hydroxide 、 2,6-二叔丁基吡啶 、 双氧水 、 三甲基铝 、 三正丁基氢锡 、 二甲基氯化铝 、 二异丁基氢化铝 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 29.0h， 生成 (2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-3,5,9-trimethyldecane
  参考文献：
  名称：

  Stereoselective synthesis of the C14–C26 fragment of the cytotoxic macrolide FD-891

  摘要：

  A stereoselective synthesis of the C-14-C-26 fragment of the naturally occurring, cytotoxic macrolide FD-891, is described. Asymmetric Evans aldol reactions and aldehyde Brown allylations are key steps of the synthesis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.013
• 作为产物：
  描述：

  (S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-pentanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 5-<(tert-Butyldiphenylsilyl)oxy>-4-methylpentanal
  参考文献：
  名称：

  Stereoselective synthesis of the C14–C26 fragment of the cytotoxic macrolide FD-891

  摘要：

  A stereoselective synthesis of the C-14-C-26 fragment of the naturally occurring, cytotoxic macrolide FD-891, is described. Asymmetric Evans aldol reactions and aldehyde Brown allylations are key steps of the synthesis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.013

文献信息

• A synthetic approach towards octalactin A, based on the stereoselective reduction of α,β-unsaturated ketones
  作者：Jordi Bach、Ramon Berenguer、Jordi Garcia、Jaume Vilarrasa

  DOI：10.1016/0040-4039(95)00498-2

  日期：1995.5

  enantioselective synthesis of the C3C9 fragment of Octalactin A and studies aimed at the conversion of Octalactin B into Octalactin A are described, which are based on the borane-mediated reduction of α,β-unsaturated ketones catalysed by B-methyl-4,5,5-triphenyl-1,3,2-oxaza-borolidines (9). A comparative study of the reduction of 2-methylnon-1-en-3-one (10) —a model of the Octalactin-A C3C9 moiety— with

  描述了一种有效的对映体，其八聚肌动蛋白A的C3C9片段的合成以及旨在将八聚肌动蛋白B转化为八聚肌动蛋白A的研究，其研究是基于硼烷介导的B-甲基-催化的α，β-不饱和酮的还原。4,5,5-三苯基-1,3,2-氧杂氮硼烷（9）。还进行了使用不同的手性试剂还原2-甲基non-1-en-3-one（10）的比较研究-Octalactin-AC3C9部分的模型。
• Furan derivatives, method of synthesis and uses thereof
  申请人：Neuropharma S.A.

  公开号：EP1939191A1

  公开（公告）日：2008-07-02

  The present invention relates to furan derivatives of formula (I), their method of synthesis and uses thereof. Concretely, the compounds disclosed have proved to be inhibitors of glycogen synthase kinase 3β, GSK-3 β, which is known to be involved in different disease and conditions, such as Alzheimer's disease or non-insulin dependent diabetes mellitus. The present invention also relates to pharmaceutical compositions comprising the same. Further, the present invention is directed to the use of the compounds in the manufacture of a medicament for the treatment and/or prevention of a GSK-3 mediated disease or condition.

  本发明涉及式(I)的呋喃衍生物，其合成方法及用途。具体来说，所披露的化合物已被证明是糖原合成酶激酶3β（GSK-3β）的抑制剂，GSK-3β已知参与不同疾病和病况，如阿尔茨海默病或非胰岛素依赖型糖尿病。本发明还涉及包含这些化合物的药物组合物。此外，本发明旨在将这些化合物用于制造治疗和/或预防GSK-3介导的疾病或病况的药物。
• Total synthesis of tetronomycin
  作者：Kozo Hori、Naotsuka Hikage、Atsushi Inagaki、Shuho Mori、Keiichi Nomura、Eiichi Yoshii

  DOI：10.1021/jo00036a026

  日期：1992.5

  The first total synthesis of (+)-tetronomycin (1), a novel tetronic acid ionophore antibiotic, has been achieved through the synthesis and assemblage of the four cyclic segments 4, 5, 7, and 8. Construction of the C5-C-13 cyclohexyl portion 5 involves as the key step either a Beckmann fragmentation of the bicyclic ketone oxime 45 or an L-Selectride-mediated reductive annulation of the nona-2,7-dienoate 53. The C-14-C28 polyether fragment 6 was constructed by a BF3-catalyzed coupling reaction of the C-14-C22 allylsilane 7 and the C23-C28 tetrahydrofuran 8 which were derived, respectively, from L-ascorbic acid or (R)-3-hydroxyisobutyrate and L-rhamnal. The union of 5 and 6 by an aldol condensation, followed by photoisomerization of the derived diastereomeric alpha,beta-unsaturated esters, provided (Z)-61, which was converted to the aldehyde 63. Subsequent acylation of the tetronate 4 with 63 via an aldol reaction-oxidation sequence afforded the protected tetronomycin 64. Final deprotection provided synthetic tetronomycin, which was characterized as its sodium salt.