(S)-tert-butyl 4-[(R,Z)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxybut-2-en-1-yl]-2,2-dimethyloxazolidine-3-carboxylate | 1011247-58-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-tert-butyl 4-[(R,Z)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxybut-2-en-1-yl]-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: (S)-4-[(Z)-(R)-4-(tert-butyldimethylsilanyloxy)-1-hydroxybut-2-enyl]-2',2'-dimethyloxazolidine-3'-carboxylic acid tert-butyl ester；tert-butyl (4S)-4-[(Z,1R)-4-[tert-butyl(dimethyl)silyl]oxy-1-hydroxybut-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1011247-58-7
• 化学式: C₂₀H₃₉NO₅Si
• 分子量: 401.619
• InChiKey: BYFABFZOBPPXRZ-YSANFCEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 4-[(R,Z)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxybut-2-en-1-yl]-2,2-dimethyloxazolidine-3-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以97%的产率得到(S)-tert-butyl 4-((R,Z)-1,4-dihydroxy-but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of Boc-protected norfuranomycins

  摘要：

  Garner's aldehyde is a suitable precursor for the synthesis of both isomers of Boc-protected epi-norfuranomycin. We demonstrate the utility of trisyl chloride as an effective leaving group in the dihydrofuran formation step. We also show that TEMPO/BAIB is an effective oxidant for a-amino alcohols avoiding epimerization of the labile a-proton of the product aldehyde. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.007
• 作为产物：
  描述：

  叔丁基二甲基(2-丙炔氧基)硅烷 在 六甲基磷酰三胺 、 正丁基锂 、 氢气 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 12.0h， 生成 (S)-tert-butyl 4-[(R,Z)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxybut-2-en-1-yl]-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  (5R,6S)-tert-butyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate 的简明合成

  摘要：

  (5 R,6 S)-叔丁基 5-乙酰氧基-6-(羟甲基)-5,6-二氢吡啶-1(2 H)-羧酸酯 1 的有效合成，这是各种多羟基化哌啶的常见中间体。从加纳醛开始的六个步骤，总产率为 32%。关键步骤包括非对映选择性亲核加成和分子内环化。(5 R,6 S)-叔丁基 5-乙酰氧基-6-(羟甲基)-5,6-二氢吡啶-1(2 H)-羧酸盐是合成 1-脱氧-L-甘露尻霉素的常见前体， 1-脱氧-L-idonojirimycin、L-fagomycin 和相关类似物。

  DOI：

  10.3998/ark.5550190.0014.218

文献信息

• Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers viaη3-allylpalladium intermediates
  作者：Mikko Passiniemi、Ari M. P. Koskinen

  DOI：10.1039/c0ob00643b

  日期：——

  A short route for the synthesis of Pachastrissamine (Jaspine B), an anhydrosphingosine derivative, and all three of its diastereomers is presented. The route consists of only 9 steps from the commercially available Garner's aldehyde. The furan framework is formed via an η3-allylpalladium intermediate.

  合成以下物质的捷径 Pachastrissamine （茉莉花B），脱水鞘氨醇衍生物及其所有三个非对映异构体。该路线仅由市售Garner醛中的9个步骤组成。呋喃框架形成经由一个η 3 π-烯丙基中间体。
• Stereoselective total synthesis of pachastrissamine (jaspine B)
  作者：Mikko Passiniemi、Ari M.P. Koskinen

  DOI：10.1016/j.tetlet.2007.12.014

  日期：2008.2

  A short total synthesis of the cytotoxic natural product pachastrissamine is described. The synthesis includes eight steps starting from Garner's aldehyde and proceeds in 20% overall yield. Pd(0)-mediated intramolecular cyclisation and Ru-mediated cross-metathesis are the key reactions in this sequence. (c) 2007 Elsevier Ltd. All rights reserved.
• A concise synthesis of (5R,6S)-tert-butyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate
  作者：S. Ramalingam、Ankushkumar D. Bhise、Krishanu Show、Pradeep Kumar

  DOI：10.3998/ark.5550190.0014.218

  日期：——

  efficient synthesis of (5 R,6 S)-tert -butyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine- 1(2 H)-carboxylate 1, a common intermediate for various polyhydroxylated piperidines is reported in six steps with 32% overall yield starti ng from Garner's aldehyde. The key steps include the diastereoselective nucleophilic additio n and intramolecular cyclization. (5 R,6 S)-tert - butyl 5-acetoxy-6-(hydroxymethyl)-5

  (5 R,6 S)-叔丁基 5-乙酰氧基-6-(羟甲基)-5,6-二氢吡啶-1(2 H)-羧酸酯 1 的有效合成，这是各种多羟基化哌啶的常见中间体。从加纳醛开始的六个步骤，总产率为 32%。关键步骤包括非对映选择性亲核加成和分子内环化。(5 R,6 S)-叔丁基 5-乙酰氧基-6-(羟甲基)-5,6-二氢吡啶-1(2 H)-羧酸盐是合成 1-脱氧-L-甘露尻霉素的常见前体， 1-脱氧-L-idonojirimycin、L-fagomycin 和相关类似物。
• Enantioselective synthesis of Boc-protected norfuranomycins
  作者：Mikko Passiniemi、Ari M.P. Koskinen

  DOI：10.1016/j.tetlet.2011.10.007

  日期：2011.12

  Garner's aldehyde is a suitable precursor for the synthesis of both isomers of Boc-protected epi-norfuranomycin. We demonstrate the utility of trisyl chloride as an effective leaving group in the dihydrofuran formation step. We also show that TEMPO/BAIB is an effective oxidant for a-amino alcohols avoiding epimerization of the labile a-proton of the product aldehyde. (C) 2011 Elsevier Ltd. All rights reserved.