isobutyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 137100-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: isobutyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-(2-methylpropoxy)-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 137100-81-3
• 化学式: C₁₄H₂₂O₆
• 分子量: 286.325
• InChiKey: GCWXWGRIJFYBIY-MJBXVCDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  isobutyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 甲醇 、 sodium methylate 作用下， 生成 C₁₀H₁₈O₄
  参考文献：
  名称：

  2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies

  摘要：

  The alarming resurgence of tuberculosis (TB) underlines the urgent need for development of new and potent anti-TB drugs. Towards this goal we herein report the design and synthesis of 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents. These easily accessible, small molecules were found to exhibit in vitro activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.78 mu g/mL to 25 mu g/mL. A detailed SAR study on these hex-2-enopyranosid-4-uloses led to the identification of compound 5g (5007-724) which on the basis of low MIC (0.78 mu g/mL-M. tuberculosis H37Rv; 1.56 mu g/mL-MDR, SDR strains of M. tuberculosis; 0.78 mu g/mL-inhibition of intracellular replication of M. tuberculosis) and SI value of 13.5 has been identified as a promising lead molecule. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.002
• 作为产物：
  描述：

  ((2R,3S)-3-acetoxy-6-hydroxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate 在 吡啶 、 四(三苯基膦)钯 、 三苯基膦 、 丙二酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 isobutyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Engelbrecht, Gerhardus J.; Holzapfel, Cedric W., Heterocycles, 1991, vol. 32, # 7, p. 1267 - 1272

  摘要：

  DOI：

文献信息

• A Highly Efficient Magnetic Iron(III) Nanocatalyst for Ferrier Rearrangements
  作者：Youxian Dong、Zekun Ding、Hong Guo、Le Zhou、Nan Jiang、Heshan Chen、Saifeng Qiu、Xiaoxia Xu、Jianbo Zhang

  DOI：10.1055/s-0037-1611855

  日期：2019.7

  A novel and highly efficient magnetic Fe3O4@C@Fe(III) core–shell catalyst, in which the carbon shell was prepared from lotus leaf, was fabricated. This nanocatalyst was successfully applied in the synthesis of a series of 2,3-unsaturated O-glycosides in excellent yields and with high selectivity, especially in the case of 2-halo O-glycosides, which differ in reactivity from nonsubstituted O-glycosides

  制备了一种新型高效的磁性 Fe3O4@C@Fe(III) 核壳催化剂，其中碳壳由荷叶制备。该纳米催化剂成功地应用于合成一系列 2,3-不饱和 O-糖苷，收率高，选择性高，特别是在反应性与未取代 O-糖苷不同的 2-卤代 O-糖苷的情况下，但以前几乎没有探索过。此外，通过施加外部磁力，催化剂可以很容易地从反应中分离出来，并且至少重复使用五次，而不会显着降低产品的产率。此外，该反应在克级规模上很容易进行，这为未来的应用提供了广阔的前景。
• 3,5-Dinitrobenzoic acid catalyzed synthesis of 2,3-unsaturated O- and S-glycosides and tetrahydropyranylation of alcohols and phenols
  作者：Naganjaneyulu Bodipati、Srinivasa Rao Palla、Venkateshwarlu Komera、Rama Krishna Peddinti

  DOI：10.1016/j.tetlet.2014.10.093

  日期：2014.12

  A simple procedure for the synthesis of 2,3-unsaturated glycosides in acetonitrile and tetrahydropyranylation of alcohols and phenols in dichloromethane in the presence of 3,5-dinitrobenzoic acid is described. A variety of alcohols and thiols are reacted with glycals to give the desired products in high yields with high α-selectivity.

  描述了一种简单的程序，用于在乙腈中合成2,3-不饱和糖苷以及在3,5-二硝基苯甲酸存在下在二氯甲烷中将醇和酚进行四氢吡喃基化。使多种醇和硫醇与缩醛反应，以高收率和高α选择性得到所需产物。
• [EN] TRANSACETALISATION PROCESS<br/>[FR] METHODE DE TRANSACETALISATION
  申请人：UNIV MONASH

  公开号：WO2005070911A1

  公开（公告）日：2005-08-04

  The invention relates to the resolution of racemic mixtures, and in particular to the separation of enantiomers of chiral alcohols utilising recyclable chiral auxiliaries. The present invention also relates to a process for preparing these recyclable chiral auxiliaries using an enantiomerically pure alcohol.

  这项发明涉及手性混合物的分离，特别是利用可回收手性辅助剂分离手性醇的对映体。本发明还涉及利用对映纯醇制备这些可回收手性辅助剂的方法。
• H2SO4-SiO2: Highly efficient and novel catalyst for the Ferrier-type glycosylation
  作者：Jia Fen Zhou、Xuan Chen、Qing Bing Wang、Bo Zhang、Li Yan Zhang、Abdullah Yusulf、Zhong Fu Wang、Jian Bo Zhang、Jie Tang

  DOI：10.1016/j.cclet.2010.03.013

  日期：2010.8

  Sulfuric acid immobilized on silica gel is designed as a very useful catalyst for synthesis of 2,3-unsaturated glycopyranosides. This handy, metal-free, environment friendly transformation provides high yields and α-stereoselectivities in a very few amount (<0.02 eq.) of catalyst and in short reaction times (<10 min).

  固定在硅胶上的硫酸被设计为非常有用的合成2，3-不饱和糖吡喃糖苷的催化剂。这种方便，无金属，环境友好的转化方法，只需极少量的催化剂（<0.02 eq。）和较短的反应时间（<10分钟），即可提供高收率和α-立体选择性。
• Ferric sulfate hydrate-catalyzed O-glycosylation using glycals with or without microwave irradiation
  作者：Guisheng Zhang、Qingfeng Liu、Lei Shi、Jiuxia Wang

  DOI：10.1016/j.tet.2007.10.097

  日期：2008.1

  O-glycosylation reaction, in which the substrates are not only peracetyl glycals but also perbenzyl glucals to afford the corresponding 2,3-unsaturated-O-glycosides via Ferrier rearrangement. The reaction of the perbenzyl glucal with various alcohols catalyzed by ferric sulfate hydrate (Fe2(SO4)3·xH2O) was successfully carried out to give 2,3-unsaturated d-O-glucosides with exclusive α-selectivity and

  我们已经开发了一种新颖的基于糖基的O-糖基化反应，其中底物不仅是过乙酰基糖基，而且是过苄基葡糖基，以通过Ferrier重排提供相应的2,3-不饱和-O-糖苷。成功地进行了苄基葡糖醛与水合硫酸铁（Fe 2（SO 4）3 · x H 2 O）催化的各种醇的反应，得到2,3-不饱和d- O-葡萄糖苷，具有独特的α-选择性和没有观察到加成产物2-脱氧己吡喃糖苷的形成。这是关于全烷基糖有效经历费勒重排而不是由路易斯酸催化的醇加成的首次报道。铁2（SO 4）3 · x H 2 O是一种有效，方便且对环境无害的多相催化剂。它具有较低的催化负荷，可回收利用，且活性没有明显降低。