methyl 4,5-O-ethylpropylidene-3-dehydro-4-epi-shikimate | 374687-81-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,5-O-ethylpropylidene-3-dehydro-4-epi-shikimate
• 英文别名: methyl 4,5-O-isopentylidene-3-dehydro-4-epi-shikimate；methyl (3aR,7aR)-2,2-diethyl-7-oxo-4,7a-dihydro-3aH-1,3-benzodioxole-5-carboxylate
• CAS: 374687-81-7
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: SHUJAAHDFMRHQF-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4,5-O-ethylpropylidene-3-dehydro-4-epi-shikimate 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 13.5h， 生成 (1R,2S,3S)-3-O-benzyl-5-(benzyloxymethyl)-1,2-ethylpropylidene-4-cyclohexene-1,2,3-triol
  参考文献：
  名称：

  A New Synthesis of Valienamine¹

  摘要：

  DOI：

  10.1021/jo010202t
• 作为产物：
  描述：

  methyl 3,4-O-ethylpropylidene-5-dehydroquinate 在 吡啶 、 三氯氧磷 作用下， 以99%的产率得到methyl 4,5-O-ethylpropylidene-3-dehydro-4-epi-shikimate
  参考文献：
  名称：

  A New Synthesis of Valienamine¹

  摘要：

  DOI：

  10.1021/jo010202t

文献信息

• [EN] COMPOUNDS AND METHODS FOR TREATMENT OF INFLUENZA<br/>[FR] COMPOSÉS ET MÉTHODES POUR LE TRAITEMENT DU VIRUS INFLUENZA
  申请人：UNIV FRASER SIMON

  公开号：WO2010075636A1

  公开（公告）日：2010-07-08

  The present invention provides in part a compound of Formula (I) or a pharmaceutically- acceptable salt or stereoisomer thereof: where R1 is selected from the group consisting of a substituted triazole group, a guanidine group, a urea group, a thiourea group, an amidine group, and N3; and R2 is selected from the group consisting of H, Me, Et and an amino acid, and methods and uses thereof.

  本发明部分提供了一种化合物，其化学式为（I）或其药用盐或立体异构体：其中R1选自以下组：取代三唑基团、胍基团、脲基团、硫脲基团、酰胺基团和N3；R2选自以下组：H、Me、Et和氨基酸，以及其方法和用途。
• Carbocycles Related to Oseltamivir as Influenza Virus Group-1-Specific Neuraminidase Inhibitors. Binding to N1 Enzymes in the Context of Virus-like Particles
  作者：Sankar Mohan、Sarah McAtamney、Thomas Haselhorst、Mark von Itzstein、Brian Mario Pinto

  DOI：10.1021/jm100822f

  日期：2010.10.28

  We report here the exploitation of the 150-cavity in the active sites of group-1 neuraminidases for the design of new triazole-containing carbocycles related to oseltamivir. Inhibition studies with virus-like particles (VLPs) containing the influenza virus neuraminidase-1 (NI) activity indicate that several candidates are inhibitors, with K(i) values in the 10(-5)-10(-8) M range. In contrast, a known candidate that preserves the free amino group and a new candidate containing a guanidine function are better inhibitors, with K(i) values of 1.5 x 10(-9) and 4.6 x 10(-10) M, respectively. The most active inhibitor of the N1 enzyme in the triazole series was selective for the N1 class and showed significantly less inhibition (K(i) = 2.6 mu M vs 0.07 mu M) of the free influenza virus neuraminidase-2 (N2). In addition, saturation transfer difference (STD) NMR spectroscopic studies with this compound and the VLPs show that the entire molecule forms contacts with residues in the active site. These data taken together support our proposed binding mode in which the active site and the adjoining 150-cavity are both occupied.
• [2+2] Photoadditions with chiral 2,5-cyclohexadienone synthons
  作者：Gordon L. Lange、Craig C. Humber、Jeffrey M. Manthorpe

  DOI：10.1016/s0957-4166(02)00339-7

  日期：2002.7

  Three chiral 2,5-cyclohexadienone synthons bearing different chiral auxiliaries were examined in [2+2] photoadditions with cyclopentene. Regeneration of the 'masked' double bond in the adducts resulted in the preparation of optically active 5-4-6 adducts. The enantiomeric purity of each adduct was found to be >95% using comparative C-13 NMR analysis of the appropriate ketals. The asymmetry induced in the cycloaddition step of our methodology indicated that the facial selectivity was directly correlated to the degree of steric bulk of the chiral auxiliary oil the synthon. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A New Synthesis of Valienamine¹
  作者：Stanton H.-L. Kok、C. C. Lee、Tony K. M. Shing

  DOI：10.1021/jo010202t

  日期：2001.10.1