methyl (3R)-4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate | 159801-08-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (3R)-4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate
• 英文别名: methyl (3R)-4-[tert-butyl(diphenyl)silyl]oxy-3-hydroxybutanoate
• CAS: 159801-08-8
• 化学式: C₂₁H₂₈O₄Si
• 分子量: 372.536
• InChiKey: IYARNAWKJBPAJQ-QGZVFWFLSA-N

物化性质

• 熔点：
  65-72 °C
• 沸点：
  448.4±45.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (3R)-4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate 在 咪唑 、 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Convergent synthesis of the C31C46 domain of the phorboxazole natural products

  摘要：

  A convergent synthesis of the C31-C46 domain of the phorboxazole natural products has been developed. This involved the preparation of a C39-C46 dienyl iodide and a C31-C37 aldehyde, followed by their CrCl2-mediated coupling and final installation of the C46 (E)-vinyl bromide via an alkyne hydrostannation-bromination sequence. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10519-6
• 作为产物：
  描述：

  D-苹果酸二甲酯 在 咪唑 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 methyl (3R)-4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate
  参考文献：
  名称：

  从 D-(+)-苹果酸中简明全合成 (-)-Erinapyrone B

  摘要：

  摘要 已经通过七个步骤实现了从市售 D-(+)-苹果酸方便且简便地对映选择性合成 (-)-erinapyrone B。该合成的关键步骤之一是在催化量的对甲苯磺酸 (p-TsOH) 存在下，钯 (II) 介导的瓦克型氧化环化的一锅反应，该反应已被证明是有效的用于通过对映体富集的二酮羟基中间体从相应的对映体纯 β-羟基烯酮制备对映体纯 2,3-二氢-4H-吡喃-4-酮。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要

  DOI：

  10.1080/00397911.2013.817017

文献信息

• Enantiospecific and diastereoselective synthesis of cis monobactams through electrophilic amination of chiral 3-hydroxyesters
  作者：Luca Banfi、Giuseppe Cascio、Giuseppe Guanti、Elso Manghisi、Enrica Narisano、Renata Riva

  DOI：10.1016/s0040-4020(01)89308-x

  日期：1994.1

  efficient entry into cis monobactams starting from β -hydroxyesters is reported. This preparation is based on the stereoselective “electrophilic amination” of β-hydroxyester dianions and on Miller's biomimetic synthesis of the β-lactam nucleus. By this route, key intermediates for the preparation of pharmacologically important cis aztreonam 2 and carumonam 3 were prepared.

  据报道，从β-羟基酯开始新的有效进入顺式单bactams的方法。该制备基于β-羟基酯二价阴离子的立体选择性“亲电胺化”和β-内酰胺核的米勒仿生合成。通过这种途径，制备了用于制备具有药理学意义的顺式氨曲南2和卡鲁米南3的关键中间体。
• Synthesis of the Macrocyclic Core of Laulimalide
  作者：Ian Paterson、Chris De Savi、Matthew Tudge

  DOI：10.1021/ol000342+

  日期：2001.1.1

  functionalized macrocyclic core of the novel microtubule-stabilizing agent, laulimalide, has been completed. Efficient macrolactonization was achieved by a Mitsunobu reaction, installing the sensitive (Z)-enoate, and macrocyclic stereocontrol was then exploited to introduce the methyl group and trans-epoxide.

  [图：见正文]已完成3的立体选择性合成，该合成对应于新型微管稳定剂laulimalide的功能齐全的大环核心。通过Mitsunobu反应（安装敏感的（Z）-烯酸酯）可实现有效的大环内酯化，然后利用大环立体控制引入甲基和反式环氧化物。
• Total Syntheses of Amphidinolides T1, T3, and T4
  作者：J. Stephen Clark、Filippo Romiti

  DOI：10.1002/anie.201305467

  日期：2013.9.16

  Concise and high‐yielding total syntheses of amphidinolides T1, T3, and T4 have been completed using an alkynyl macrolactone as a common late‐stage intermediate. The required α‐hydroxy ketone motif was installed by sequential alkyne hydrosilylation, epoxidation, and Fleming–Tamao oxidation. An oxonium ylide rearrangement formed the trisubstituted tetrahydrofuran core found in the natural products.

  使用炔基大内酯作为常见的后期中间体，可以完成简明高效的两性化合物T1，T3和T4的合成。所需的α-羟基酮基序通过依次进行的炔烃氢化硅烷化，环氧化和Fleming-Tamao氧化来安装。氧鎓叶立德重排形成天然产物中发现的三取代四氢呋喃核。
• Macrocyclic Bisindolylmaleimides:  Synthesis by Inter- and Intramolecular Alkylation
  作者：Margaret M. Faul、Leonard L. Winneroski、Christine A. Krumrich、Kevin A. Sullivan、James R. Gillig、David A. Neel、Christopher J. Rito、Michael R. Jirousek

  DOI：10.1021/jo971980h

  日期：1998.3.1

  Macrocyclic bisindolylmaleimides 1-4 have been identified as competitive reversible inhibitors of PKC beta(1) and beta(2) and are being advanced to the clinic for evaluation as a treatment of retinopathy associated with diabetic complications. Highly convergent and stereoselective syntheses of 1-4 have been developed. The key synthetic step involves intermolecular alkylation of symmetrical bisindolylmaleimide 9 with chiral bisalkylating agent 8c and is amenable to the preparation of multikilogram quantities of these compounds. The synthetic sequence to 1, the most active compound, proceeds in 11 steps and 26% overall yield (>98% ee) from (R)-1-chloro-2,3-propanediol. No chromatographic purifications are required throughout the process and the final product is isolated in >97% purity after crystallization from DMF/MeOH. Synthesis of 1-4 by intramolecular alkylation proved less efficient, requiring 1? steps and affording 1-4 in lower overall yields of 6.0-8.5%.
• Efficient Synthesis of (−)-<i>trans</i>-Kumausyne via Tandem Intramolecular Alkoxycarbonylation−Lactonization
  作者：John Boukouvalas、Geneviève Fortier、Ioan-Iosif Radu

  DOI：10.1021/jo972066r

  日期：1998.2.1