4-azido-2,3-di-O-acetyl-4,6-dideoxy-α-D-glucopyranosyl trichloroacetimidate | 485809-80-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-azido-2,3-di-O-acetyl-4,6-dideoxy-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: 2,3-di-O-acetyl-4-azido-4,6-dideoxy-D-glucopyranosyl trichloroacetimidate；[(2R,3R,4S,5R,6R)-5-acetyloxy-3-azido-2-methyl-6-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl] acetate
• CAS: 485809-80-1
• 化学式: C₁₂H₁₅Cl₃N₄O₆
• 分子量: 417.633
• InChiKey: HRLWFNVIRFONEJ-PMZAMSJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-azido-2,3-di-O-acetyl-4,6-dideoxy-α-D-glucopyranosyl trichloroacetimidate 在 甲醇 、 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 、 三氟甲磺酸三甲基硅酯 、 Pd(OH)2/C 、 氢气 、 sodium methylate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， -40.0~50.0 ℃ 、1.0 MPa 条件下， 反应 32.5h， 生成 2-aminoethyl 4-(3-hydroxy-3-methylbutanamido)-4,6-dideoxy-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranoside
  参考文献：
  名称：

  合成与炭疽四糖的非甲基化的二糖类似物的免疫化学评估†

  摘要：

  炭疽四糖是一种在炭疽芽孢杆菌孢子最外表面表达的寡糖，具有三个鼠李糖酶和一种称为蔗糖的稀有糖。现已确定该基序是未来人类预防炭疽疫苗的合理组成部分。我们在此报道了从环状硫酸盐中间体合成该四糖的2 - O-去甲基化-β - D-蒽吡喃糖基- （1→3）-α - L-鼠李糖吡喃糖二糖类似物。当在BALB / c小鼠中给药时，与BSA偶联的这种二糖可诱导抗天然四糖IgG抗体反应。此外，诱导的血清与天然炭疽芽孢杆菌结合内生孢子。这些结果表明，容易适合于合成规模化的二糖类似物可以用于糖缀合物抗原制剂中。

  DOI：

  10.1039/c2ob26131f
• 作为产物：
  描述：

  methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 在 吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 草酰氯 、 三氟甲磺酸酐 、 硫酸 、 乙酸肼 、 对甲苯磺酸 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 4-azido-2,3-di-O-acetyl-4,6-dideoxy-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin

  摘要：

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

  DOI：

  10.1021/jo035290r

文献信息

• Synthesis of novel aminoglycosides via allylic azide rearrangement for investigating the significance of 2′-amino group
  作者：Jianjun Zhang、Anthony Litke、Katherine Keller、Ravi Rai、Cheng-Wei Tom Chang

  DOI：10.1016/j.bmc.2010.01.027

  日期：2010.2

  Using allylic azide rearrangement, a convenient method has been developed for the synthesis of 2′,3′-dideoxyaminoglycosides that are, otherwise, difficult to be prepared. The antibacterial activity of these novel aminoglycosides also confirms the indispensable role of 2′-NH2 group for both neomycin and kanamycin classes of aminoglycosides. A novel structural motif containing the hexylaminocarbonyl

  使用烯丙基叠氮化物重排，已经开发了方便的方法来合成否则难以制备的2'，3'-二脱氧氨基糖苷。这些新型氨基糖苷类的抗菌活性也证实了2'-NH 2基团对于新霉素类和卡那霉素类氨基糖苷类都起着不可或缺的作用。在2'，3'-二脱氧亚胺的O -5和/或O -6处含有己氨基羰基的新型结构基序可以导致产生新的抗药性氨基糖苷。
• Design and Synthesis of Pyrankacin:  A Pyranmycin Class of Broad-Spectrum Aminoglycoside Antibiotic
  作者：Ravi Rai、Hsiao-Nung Chen、Przemyslaw G. Czyryca、Jie Li、Cheng-Wei Tom Chang

  DOI：10.1021/ol0529750

  日期：2006.3.2

  A novel broad-spectrum aminoglycoside antibiotic, pyrankacin, has been prepared. In addition to the synthetic innovation in dideoxygenation and regioselective Staudinger reduction, we have obtained prominent antibacterial activity against several clinically important pathogens in the course of this work.

  已经制备了一种新型的广谱氨基糖苷类抗生素吡喃卡星。除了在双脱氧和区域选择性施陶丁格还原方面的合成创新外，我们在这项工作过程中还获得了对几种临床上重要病原体的显着抗菌活性。
• Novel anti bacterial compounds
  申请人：Chang Tom Cheng-Wei

  公开号：US20060234961A1

  公开（公告）日：2006-10-19

  The invention relates to novel paranmycin compounds that have activity against gram positive and gram negative bacteria, preferably bacteria that are resistant to other antibiotics. Paranmycins are of the general formula

  本发明涉及新型的帕拉霉素化合物，其具有对革兰氏阳性和革兰氏阴性细菌的活性，更好地对抗其他抗生素耐药的细菌。帕拉霉素的一般化学式为：
• Pyranmycins, a Novel Class of Aminoglycosides with Improved Acid Stability:  The SAR of <scp>d</scp>-Pyranoses on Ring III of Pyranmycin
  作者：Cheng-Wei Tom Chang、Yu Hui、Bryan Elchert、Jinhua Wang、Jie Li、Ravi Rai

  DOI：10.1021/ol0269042

  日期：2002.12.1

  The synthesis of a novel class of aminoglycosides, pyranmycins, is reported along with the structure activity relationship (SAR) of their antibacterial activity against Escherichia coli. Two pyranmycins show prominent activity (9 muM). Pyranmycins also manifest superior stability in acidic media. The SAR information will lead to the future designs of pyranmycin against drug resistant bacteria.
• Synthesis and antibacterial activity of pyranmycin derivatives with N-1 and O-6 modifications
  作者：Jie Li、Fang-I Chiang、Hsiao-Nung Chen、Cheng-Wei Tom Chang

  DOI：10.1016/j.bmc.2007.08.059

  日期：2007.12

  Continuing from our ongoing effort in modifying aminoglycoside antibiotics with the goal of counteracting drug resistant bacteria, we have further derivatized pyranmycin, a neomycin class aminoglycoside antibiotic, with modifications at O-6 and N-1 positions. The revealed SAR results demonstrated that the antibacterial activity of pyranmycin can be modulated by different acylic substituents at O-6. Among these results, the 6-O-aminoethyl derivative, JT050, showed effective activity against resistant strain Escherichia coli (pTZ19U-3) and E. coli (pSF815), which provides insight into further structural modi. cations. (c) 2007 Elsevier Ltd. All rights reserved.