3,2'-di-N-benzyloxycarbonyl-1,6:6',4'-N,O-carbonyl-neamine | 66787-82-4

• 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: 3,2'-di-N-benzyloxycarbonyl-1,6:6',4'-N,O-carbonyl-neamine
• 英文别名: O⁴-(6-amino-2-benzyloxycarbonylamino-N⁶,O⁴-carbonyl-α-D-2,6-dideoxy-glucopyranosyl)-N³-benzyloxycarbonyl-N¹,O⁶-carbonyl-1D-2-deoxy-streptamine
• CAS: 66787-82-4
• 化学式: C₃₀H₃₄N₄O₁₂
• 分子量: 642.62
• InChiKey: HSSLFSCSWMRUII-YRLDIHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  212.24
• 氢给体数：
  6.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3,2'-di-N-benzyloxycarbonyl-1,6:6',4'-N,O-carbonyl-neamine 在 吡啶 、 氨 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以88%的产率得到3,2'-di-N-benzyloxycarbonyl-1-N-(aminoformyl)-6',4'-N,O-carbonyl-neamine
  参考文献：
  名称：

  Regioselective modification of amino groups in aminoglycosides based on cyclic carbamate formation

  摘要：

  Conditions for regioselective introduction of cyclic carbamate into per-N-Cbz neamine and per-N-Cbz kanamycin A have been found. The position and number of cyclic Carbamate formed in these two aminoglycosides was controllable. On the base of selective cyclic carbamate formation, regioselective modification on N-1, N-6' or both amino groups in neat-nine, and on N-6', N-3 '' or both amino groups in kanamycin A was achieved by ring-opening reaction with amines. A new neamine dimer linked at the N-1 was also synthesized with this method. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.022
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.75h， 以0.23 g的产率得到3,2'-di-N-benzyloxycarbonyl-1,6:6',4'-N,O-carbonyl-neamine
  参考文献：
  名称：

  Regioselective modification of amino groups in aminoglycosides based on cyclic carbamate formation

  摘要：

  Conditions for regioselective introduction of cyclic carbamate into per-N-Cbz neamine and per-N-Cbz kanamycin A have been found. The position and number of cyclic Carbamate formed in these two aminoglycosides was controllable. On the base of selective cyclic carbamate formation, regioselective modification on N-1, N-6' or both amino groups in neat-nine, and on N-6', N-3 '' or both amino groups in kanamycin A was achieved by ring-opening reaction with amines. A new neamine dimer linked at the N-1 was also synthesized with this method. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.022

文献信息

• Aminoglycoside antibiotics. 1. Regiospecific partial syntheses of ribostamycin and butirosin B
  作者：Virendra Kumar、William A. Remers

  DOI：10.1021/jo00411a014

  日期：1978.8
• Synthesis of a Neamine Dimer Targeting the Dimerization Initiation Site of HIV-1 RNA
  作者：Anne Bodlenner、Aurélien Alix、Jean-Marc Weibel、Patrick Pale、Eric Ennifar、Jean-Christophe Paillart、Philippe Walter、Roland Marquet、Philippe Dumas

  DOI：10.1021/ol701760k

  日期：2007.10.1

  [GRAPHICS]A neamine dimer designed to bind to a specific sequence of HIV-1 RNA has been synthesized. Starting from neomycin B (1), a five-step synthesis efficiently provided a key protected neamine monomer 6 (28%). From the latter, coupling reactions with activated diacids gave dimers. After deprotection, a neamine dimer was obtained as the hexachlorohydrate salt 15 with 13% overall yield over nine steps.