5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-[N'-(tertbutoxycarbonyl)thiourea]-3,4,5-trideoxy-D-glycero-D-galactonon-2-enonic acid methyl ester | 1037587-60-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-[N'-(tertbutoxycarbonyl)thiourea]-3,4,5-trideoxy-D-glycero-D-galactonon-2-enonic acid methyl ester
• 英文别名: methyl (2R,3R,4S)-3-acetamido-4-[(2-methylpropan-2-yl)oxycarbonylcarbamothioylamino]-2-[(1S,2R)-1,2,3-triacetyloxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 1037587-60-2
• 化学式: C₂₄H₃₅N₃O₁₂S
• 分子量: 589.621
• InChiKey: ASRPNNJVWMRYKG-CJSSEVFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  226
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-[N'-(tertbutoxycarbonyl)thiourea]-3,4,5-trideoxy-D-glycero-D-galactonon-2-enonic acid methyl ester 、 N-叔丁氧羰基-1,4-丁二胺 在 三乙胺 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以74%的产率得到5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-[N'-(tertbutoxycarbonyl)-N''-(4-tert-butoxycarbonylaminobutyl)guanidino]-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester
  参考文献：
  名称：

  Analogs of zanamivir with modified C4-substituents as the inhibitors against the group-1 neuraminidases of influenza viruses

  摘要：

  Unlike the group-2 neuraminidase, the group-1 neuraminidase of influenza virus possesses a flexible loop (the 150-loop) and a cavity (the 150-cavity) adjacent to the active site, and renders a conformational change from the 'open' form to the 'closed' form on binding with substrate (sialo-glycoprotein) or inhibitor (e.g., zanamivir). Zanamivir derivative 8a having an extended (piperazinocarbonyl)propyl substituent at the internal N-position of the guanidino group is designed as a possible inhibitor on the basis of computer docking to the open form of N1 subtype neuraminidase. Indeed, compound 8a exhibits strong neuraminidase inhibition and good anti-influenza activity against H1N1 virus with IC(50) = 2.15 mu M and EC(50) = 0.77 mu M, respectively. This study may provide a clue to future design of better group-1 neuraminidase inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.010
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以3.23 g的产率得到5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-[N'-(tertbutoxycarbonyl)thiourea]-3,4,5-trideoxy-D-glycero-D-galactonon-2-enonic acid methyl ester
  参考文献：
  名称：

  Analogs of zanamivir with modified C4-substituents as the inhibitors against the group-1 neuraminidases of influenza viruses

  摘要：

  Unlike the group-2 neuraminidase, the group-1 neuraminidase of influenza virus possesses a flexible loop (the 150-loop) and a cavity (the 150-cavity) adjacent to the active site, and renders a conformational change from the 'open' form to the 'closed' form on binding with substrate (sialo-glycoprotein) or inhibitor (e.g., zanamivir). Zanamivir derivative 8a having an extended (piperazinocarbonyl)propyl substituent at the internal N-position of the guanidino group is designed as a possible inhibitor on the basis of computer docking to the open form of N1 subtype neuraminidase. Indeed, compound 8a exhibits strong neuraminidase inhibition and good anti-influenza activity against H1N1 virus with IC(50) = 2.15 mu M and EC(50) = 0.77 mu M, respectively. This study may provide a clue to future design of better group-1 neuraminidase inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.010

文献信息

• N,N′-Di-Boc-Substituted Thiourea as a Novel and Mild Thioacylating Agent Applicable for the Synthesis of Thiocarbonyl Compounds
  作者：Biao-Lin Yin、Zhao-Gui Liu、Jian-Cun Zhang、Zheng-Rong Li

  DOI：10.1055/s-0029-1219273

  日期：2010.3

  Stable and readily available N,N′-di-Boc-substituted thiourea, when activated with trifluoroacetic acid anhydride, was used as a novel thioacylating agent. Through the thioacylation of nucleophiles, such as amines, alcohols, thiols, sodium benzene­thiolate, and sodium malonates with N,N′-di-Boc-substituted thiourea, a series of thiocarbonyl compounds were prepared under mild conditions with good chemical selectivity and functional group tolerance.

  稳定且易于获得的N,N′-双-Boc取代硫脲，在三氟乙酸酐活化下，被用作一种新型硫代酰化剂。通过对亲核试剂如胺、醇、硫醇、苯硫醇钠和丙二酸钠与N,N′-双-Boc取代硫脲的硫代酰化反应，一系列硫代羰基化合物在温和条件下以良好的化学选择性和官能团耐受性被制备出来。
• An efficient method for the synthesis of disubstituted thioureas via the reaction of N,N′-di-Boc-substituted thiourea with alkyl and aryl amines under mild conditions
  作者：Biaolin Yin、Zhaogui Liu、Mingjun Yi、Jiancun Zhang

  DOI：10.1016/j.tetlet.2008.03.158

  日期：2008.5

  An efficient method for the synthesis of disubstituted thioureas via the reaction of N,N′-di-Boc-substituted thiourea 5 with alkyl and aryl amines under mild conditions has been developed. In the presence of NaH as a base, trifluoroacetic anhydride (TFAA) reacted with 5 providing intermediate 6, which then reacted with amines giving thioureas 7 in excellent yields. This reaction conditions tolerated

  已经开发了通过N，N′-二-Boc-取代的硫脲5与烷基和芳基胺在温和的条件下反应合成二取代的硫脲的有效方法。在作为碱的NaH存在下，三氟乙酸酐（TFAA）与5反应生成中间体6，然后与胺反应生成硫脲7的产率很高。该反应条件容许其他官能团，例如酰胺，酯，烯醇醚和羟基。