(2S,3R)-2,3-epoxy-4-(tert-butyldimethylsilyloxy)butanal | 859216-20-9

• 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: (2S,3R)-2,3-epoxy-4-(tert-butyldimethylsilyloxy)butanal
• 英文别名: (2S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]oxirane-2-carbaldehyde
• CAS: 859216-20-9
• 化学式: C₁₀H₂₀O₃Si
• 分子量: 216.352
• InChiKey: ZZEAXSVHLYHJBB-RKDXNWHRSA-N

物化性质

• 沸点：
  261.8±25.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2,3-epoxy-4-(tert-butyldimethylsilyloxy)butanal 在 C₂₇H₃₄O₅Si 、 红铝 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 2.25h， 生成
  参考文献：
  名称：

  十氢化萘和立体异构体类似物的烯烃跨复分解方法

  摘要：

  据报道，天然产物（-）-depudecin的新的全合成，这是一种独特的，尚未开发的组蛋白脱乙酰基酶（HDAC）抑制剂。合成的关键特征是利用了烯烃的交叉复分解策略，与我们以前的线性合成方法相比，该策略提供了一种有效且改进的获得天然氘代十丁烯的途径。我们开发的合成策略以其简洁和收敛性为特征，被用于制备10- Epi衍生物和地普丁的对映异构体，它们代表了有趣的立体异构体类似物，用于结构-活性关系研究。

  DOI：

  10.1021/acs.joc.7b00424
• 作为产物：
  描述：

  4-(tert-butyldimethylsilyloxy)-2-butyn-1-ol 在 叔丁基过氧化氢 、 草酰氯 、 N,N-Diisopropyltryptamine 、 titanium(IV)isopropoxide 、 二甲基亚砜 、 红铝 作用下， 以 四氢呋喃 、 癸烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 25.75h， 生成 (2S,3R)-2,3-epoxy-4-(tert-butyldimethylsilyloxy)butanal
  参考文献：
  名称：

  Fluorosugars: An improved synthesis of the 2,3,4-trideoxy-2,3,4-trifluoro hexose analogue of d-glucose

  摘要：

  An improved synthetic route for the synthesis of the 2,3,4-trideoxy-2,3,4-trifluoro hexose analogue of D-glucose has been developed. The newly reported synthesis features improved fluorination reactions and simpler chromatographic separations. (C) 2013 Published by Elsevier B.V.

  DOI：

  10.1016/j.jfluchem.2013.06.003

文献信息

• Total Synthesis of Largazole - Devolution of a Novel Synthetic Strategy
  作者：Craig Forsyth、Bo Wang

  DOI：10.1055/s-0029-1216931

  日期：2009.9

  largazole embodies a compelling combination of a relatively simple, yet unique cyclic depsipeptide structure with remarkable levels of selective cytotoxicity against cancer cell lines versus nontransformed cells. The unique structure of largazole inspired a strategically novel and aggressive approach towards its expedient total synthesis. This involved an initial dissection into an epoxy aldehyde and an unprotected

  蓝细菌分离物拉格唑体现了相对简单而独特的环状双缩肽结构的令人信服的组合，该结构具有显着水平的针对癌细胞系和未转化细胞的选择性细胞毒性。largazole的独特结构激发了一种战略上新颖且具有侵略性的方法来实现方便的全合成。这涉及到初始分解为环氧醛和未保护的四肽，分别代表拉格唑的聚酮和多肽结构域。这些片段使用NHC介导的酰胺化成功连接，但随后通过内酯化的环状二肽的组装受到阻碍。关键联轴器的重新排序导致了largazole的成功组装。 全合成-杂环-十肽-N-杂环卡宾-噻唑啉
• First Asymmetric Total Synthesis of Synerazol, an Antifungal Antibiotic, and Determination of Its Absolute Stereochemistry
  作者：Yujiro Hayashi、Mitsuru Shoji、Takasuke Mukaiyama、Hiroaki Gotoh、Shinpei Yamaguchi、Munetaka Nakata、Hideaki Kakeya、Hiroyuki Osada

  DOI：10.1021/jo050664x

  日期：2005.7.1

  first asymmetric total synthesis of synerazol, an antifungal antibiotic, has been accomplished, allowing determination of its absolute stereochemistry. A more practical second generation route was also established. The key steps are racemization-free deprotection of a TIPS group and introduction of a methyl ether by DMD oxidation of the benzylidene moiety in a substrate having a small protecting group

  通过合成两种可能的非对映异构体，已经完成了抗真菌抗菌药合那唑的首次不对称全合成，从而可以确定其绝对立体化学。还建立了更实用的第二代路线。关键步骤是TIPS基团的无消旋脱保护和通过DMD氧化具有小的保护基团的底物中的亚苄基部分来引入甲基醚。
• Total Syntheses of the Histone Deacetylase Inhibitors Largazole and 2-<i>epi</i>-Largazole: Application of <i>N</i>-Heterocyclic Carbene Mediated Acylations in Complex Molecule Synthesis
  作者：Bo Wang、Po-Hsien Huang、Ching-Shih Chen、Craig J. Forsyth

  DOI：10.1021/jo102478x

  日期：2011.2.18

  Details of the evolution of strategies toward convergent assembly of the histone deacetylase inhibiting natural product largazole exploiting gamma,delta-unsaturated-alpha,beta-epoxy-aldehydes and a thiazole-thiazoline containing omega-amino-acid are described. The initial N-heterocyclic carbene mediated redox amidation exploying these two types of building blocks representing largazole's structural domains of distinct biosynthetic origin directly afforded the seco-acid of largazole. This was accomplished without any protecting groups resident upon either thioester bearing epoxy-aldehyde or the tetrapeptide. However, the ineffective production of largazole via the final macrolactonization led to an alternative intramolecular esterification/macrolactamization strategy employing the established two building blocks. This provided largazole along with its C2-epimer via an unexpected inversion of the alpha-stereocenter at the valine residue. The biological evaluation demonstrated that both largazole and 2-epi-largazole led to dose-dependent increases of acetylation of histone H3, indicating their potencies as class I histone deacetylase selective inhibitiors. Enhanced p21 expression was also induced by largazole and its C2 epimer. In addition, 2-epi-largazole displayed more potent activity than largazole in cell viability assays against PC-3 and LNCaP prostate cancer cell lines.