(1S,2R,3R,4S,6R)-4,6-Diazido-3-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol | 870180-36-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R,3R,4S,6R)-4,6-Diazido-3-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol
• 英文别名: (1S,2R,3R,4S,6R)-4,6-diazido-3-[(4-methoxyphenyl)methoxy]cyclohexane-1,2-diol
• CAS: 870180-36-2
• 化学式: C₁₄H₁₈N₆O₄
• 分子量: 334.335
• InChiKey: NQWVFAOTOCFTCF-MBJXGIAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  87.6
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R,4S,6R)-4,6-Diazido-3-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol 在 吡啶 、 水 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.25h， 生成 Trifluoro-methanesulfonic acid (1R,2R,3S,4R,6S)-4,6-diazido-2,3-bis-benzyloxy-cyclohexyl ester
  参考文献：
  名称：

  Novel 2,5-dideoxystreptamine derivatives targeting the ribosomal decoding site RNA

  摘要：

  The ribosomal decoding site is the target of aminoglycoside antibiotics that specifically recognize an internal loop RNA structure. We synthesized RNA-targeted 2,5-dideoxystreptamine-4-amides in which a sugar moiety in natural aminoglycosides is replaced by heterocycles. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00759-x
• 作为产物：
  描述：

  2-deoxy-1,3-diazido-5,6-O-isopropylidenestreptamine 在 sodium hydride 作用下， 以 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (1S,2R,3R,4S,6R)-4,6-Diazido-3-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol
  参考文献：
  名称：

  作为 RNA 结合配体的杂环 2-脱氧三苯乙醇胺衍生物的有效合成

  摘要：

  描述了一种合成杂环 2-脱氧链霉胺衍生物的有效策略。所得化合物从 ESI-MS RNA 结合测定中显示出良好的 RNA 结合亲和力。

  DOI：

  10.1246/cl.2003.908

文献信息

• Probing the ribosomal RNA A-site with functionally diverse analogues of paromomycin—synthesis of ring I mimetics
  作者：Stephen Hanessian、Susanta Adhikari、Janek Szychowski、Kandasmy Pachamuthu、Xiaojing Wang、Michael T. Migawa、Richard H. Griffey、Eric E. Swayze

  DOI：10.1016/j.tet.2006.10.079

  日期：2007.1

  Methods were developed to selectively cleave the 2-amino-2-deoxy-alpha-D-glucopyranosyl ring in paromomycin. The preferentially N- and O-protected products were alkylated on the liberated C4 hydroxyl group of the deoxystreptalnine subunit. Further manipulation furnished a series of aromatic, heteroaromatic, and aliphatic appendages as spatial mimics offing 1. Modest inhibitory activity was found against Staphylococcus aureus with two analogues (27 and 63), although cell-free functional transcription/translation assays were similar to paromomycin for analogue 27. (c) 2006 Elsevier Ltd. All rights reserved.
• The synthesis and 16S A-site rRNA recognition of carbohydrate-free aminoglycosides
  作者：Xiaojing Wang、Michael T. Migawa、Kristin A. Sannes-Lowery、Eric E. Swayze

  DOI：10.1016/j.bmcl.2005.08.027

  日期：2005.11

  The first carbohydrate-free aminoglycoside analogs bearing the 2-deoxystreptamine moiety were synthesized from asymmetrically protected 2-deoxystrepamine and subsequently demonstrated to have significant binding to the 16S A-site rRNA target and moderate functional activity. (c) 2005 Elsevier Ltd. All rights reserved.