1,3,2',6'-tetrakis-N-benzyloxycarbonylgentamine C_1a | 42801-36-5

• 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: 1,3,2',6'-tetrakis-N-benzyloxycarbonylgentamine C_1a
• 英文别名: 1,3,2',6'-Tetra-N-benzyloxycarbonyl-3',4'-dideoxyneamin；benzyl N-[(2R,3R,6S)-2-[(1R,2R,3S,4R,6S)-2,3-dihydroxy-4,6-bis(phenylmethoxycarbonylamino)cyclohexyl]oxy-6-(phenylmethoxycarbonylaminomethyl)oxan-3-yl]carbamate
• CAS: 42801-36-5
• 化学式: C₄₄H₅₀N₄O₁₂
• 分子量: 826.901
• InChiKey: CIYRTNRMZMHIGM-GZLBHUHZSA-N

物化性质

• 沸点：
  993.6±65.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  60.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  1,3,2',6'-tetrakis-N-benzyloxycarbonylgentamine C_1a 生成 1L-N¹-benzyloxycarbonyl-O⁶-(2,6-bis-benzyloxycarbonylamino-α-D-erythro-2,3,4,6-tetradeoxy-hexopyranosyl)-N³,O⁴-carbonyl-2-deoxy-streptamine
  参考文献：
  名称：

  UMEZAWA, HAMAO;KONDO, SHINICHI;IKEDA, DAISHIRO

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S,2R,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)tetrahydropyran-2-yl]oxy-cyclohexane-1,2-diol 、 benzyl 4,6-dimethyl-2-sulfanyl-2H-pyrimidine-1-carboxylate 生成 1,3,2',6'-tetrakis-N-benzyloxycarbonylgentamine C_1a
  参考文献：
  名称：

  UMEZAWA, HAMAO;KONDO, SHINICHI;IKEDA, DAISHIRO

  摘要：

  DOI：

文献信息

• Semisynthetic aminoglycoside antibacterials. Part 7. Synthesis of novel hexopyranosyl and hexofuranosyl derivatives of gentamine C1 and C1a
  作者：Peter J. L. Daniels、Charles E. Luce、Alan K. Mallams、James B. Morton、Surinderjit S. Saluja、Hsingan Tsai、Jay Weinstein、John J. Wright、George Detre、Masato Tanabe、Dennis M. Yasuda

  DOI：10.1039/p19810002137

  日期：——

  Acidic hydrolysis of gentamicin C1 and C1a provides ready access to the pseudodisaccharides gentamine C1 and C1a respectively. Glycosylation of tetrakis-N-benzyloxycarbonylgentamine C1 and C1a using the Koenigs–Knorr or Lemieux–Nagabhushan reactions has led to the preparation of a series of novel 6-O-α- and -β-3-amino-3-deoxy- and 2-amino-2-deoxy-D-hexopyranosyl and hexofuranosyl analogues of the gentamicins

  庆大霉素C 1和C 1a的酸性水解可分别轻松获得假二糖gentamine C 1和C 1a。使用Koenigs-Knorr或Lemieux-Nagabhushan反应的四-N-苄氧基羰基银胺C 1和C 1a的糖基化反应导致制备了一系列新型的6 - O -α-和-β-3-氨基-3-脱氧-庆大霉素的2-氨基-2-脱氧-D-己吡喃糖基和己呋喃糖基类似物。的13 C NMR代表性化合物的性质所描述和有关C-4-旋转异构体群体ö和C-6- Ò 糖苷键进行了讨论。
• Semisynthetic aminoglycoside antibacterials. Part 8. Synthesis of novel pentopyranosyl and pentofuranosyl derivatives of gentamine C1 and C1a
  作者：D. Huw Davies、Max Kugelman、Paul Lee、Charles E. Luce、Alan K. Mallams、James B. Morton、Surinderjit S. Saluja、John J. Wright、George Detre、Masato Tanabe、Dennis M. Yasuda

  DOI：10.1039/p19810002151

  日期：——

  of a variety of 6-O- and 5-O-pentopyranosyl and -pentofuranosyl derivatives from 1,3,2′,6′-tetrakis-N-benzyloxycarbonylgentamine C1a and C1 are described. These include neutral glycosides as well as 3-amino-3-deoxy- and 3-deoxy-3-methylamino-glycosides. The solution conformations of these novel semisynthetic aminoglycoside antibacterials are described.

  描述了由1,3,2'，6'-四-N-苄氧基羰基银胺C 1a和C 1合成各种6- O-和5- O-戊吡喃糖基和-戊呋喃糖基衍生物的方法。这些包括中性糖苷以及3-氨基-3-脱氧-和3-脱氧-3-甲基氨基-糖苷。描述了这些新型半合成氨基糖苷类抗菌剂的溶液构象。
• Synthesis and antibacterial activity of novel neamine derivatives
  作者：Nobuto Minowa、Yoshihisa Akiyama、Yukiko Hiraiwa、Kazunori Maebashi、Takayuki Usui、Daishiro Ikeda

  DOI：10.1016/j.bmcl.2006.09.007

  日期：2006.12

  Synthesis and activity of derivatives at the O5 or O6 positions of 1-N-((S)-4-amino-2-hydroxybutyryl)-3',4'-dideoxyneamine, which is the neamine moiety of arbekacin, were reported. Among these results, the 5-O-aminoethylaminocarbonyl derivative showed effective activity against Staphylococcus aureus expressing a bifunctional aminoglycoside-modifying enzyme AAC(6')APH(2"). (c) 2006 Elsevier Ltd. All rights reserved.