1,3,6'-tri-(tert-butoxycarbonyl)-neamine | 153953-69-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,6'-tri-(tert-butoxycarbonyl)-neamine
• 英文别名: 1,3,6'-Tri-N-(tert-butoxycarbonyl)neamine；tert-butyl N-[[(2R,3S,4R,5R,6R)-5-amino-6-[(1R,2R,3S,4R,6S)-2,3-dihydroxy-4,6-bis[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexyl]oxy-3,4-dihydroxyoxan-2-yl]methyl]carbamate
• CAS: 153953-69-6
• 化学式: C₂₇H₅₀N₄O₁₂
• 分子量: 622.714
• InChiKey: SMTLTMDETAHNMV-LNYKISQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  240
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1,3,6'-tri-(tert-butoxycarbonyl)-neamine 在 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 N-[(2R,3R,4R,5S,6R)-6-Aminomethyl-2-((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxy-cyclohexyloxy)-4,5-dihydroxy-tetrahydro-pyran-3-yl]-2-bromo-acetamide; compound with trifluoro-acetic acid
  参考文献：
  名称：

  The use of neamine as a molecular template: Inactivation of bacterial antibiotic resistance enzyme aminoglycoside 3′-phosphotransferase type IIa

  摘要：

  Aminoglycoside 3'-phosphotransferase type IIa [APH(3')-IIa] is a member of the family of bacterial aminoglycoside-modifying enzymes. Bacteria that harbor these enzymes are resistant to aminoglycoside antibiotics. Four aminoglycoside-based affinity inactivators were synthesized and were shown to be both substrates and inactivators for APH(3')-IIa. These affinity inactivators are N-bromoacetylated derivatives of neamine, an aminoglycoside antibiotic, where the bromoacetyl moiety in each was introduced regiospecifically at a different amine of the parent compound. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00633-7
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 thallium (I) ethoxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 51.0h， 生成 1,3,6'-tri-(tert-butoxycarbonyl)-neamine
  参考文献：
  名称：

  N-(tert-Butoxycarbonyloxy)-5-norbornene-endo-2,3-dicarboximide, a Reagent for the Regioselective Introduction of the tert-Butoxycarbonyl (BOC) Protective Group at Unhindered Amines: Application to Amino glycoside Chemistry

  摘要：

  DOI：

  10.1021/jo00086a055

文献信息

• Selectively guanidinylated derivatives of neamine. Syntheses and inhibition of anthrax lethal factor protease
  作者：Guan-Sheng Jiao、Ondrej Simo、Melissa Nagata、Sean O’Malley、Thomas Hemscheidt、Lynne Cregar、Sherri Z. Millis、Mark E. Goldman、Cho Tang

  DOI：10.1016/j.bmcl.2006.07.005

  日期：2006.10

  A series of mono-, di-, and tri-guanidinylated derivatives of neamine were prepared via selective guanidinylation of neamine. These molecules represent a novel scaffold as inhibitors of anthrax lethal factor zinc metalloprotease. Methods for the synthesis of these compounds are described, and structure-activity relationships among the series are analyzed. In addition, initial findings regarding the mechanism of LF inhibition for these molecules are presented. (c) 2006 Elsevier Ltd. All rights reserved.