ethyl 2,3,5-tri-O-acetyl-1-thio-D-ribofuranose | 108800-82-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2,3,5-tri-O-acetyl-1-thio-D-ribofuranose
• 英文别名: ethyl 2,3,5-tri-O-acetyl-1-thio-α/β-D-ribofuranoside；2,3,5-Triacetyl-aethylmercapto-α-D-ribofuranosid；[(2R,3R,4R)-3,4-diacetyloxy-5-ethylsulfanyloxolan-2-yl]methyl acetate
• CAS: 108800-82-4
• 化学式: C₁₃H₂₀O₇S
• 分子量: 320.364
• InChiKey: FUAHCNKSXABULR-PFGBXZAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2,3,5-tri-O-acetyl-1-thio-D-ribofuranose 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  A New Class of Branched Aminoglycosides:  Pseudo-Pentasaccharide Derivatives of Neomycin B

  摘要：

  The clinically important antibiotic neomycin B was modified at position C5" by adding one extra sugar ring in the beta-configuration, and the observed pseudo-pentasaccharides were tested against various bacterial strains, including pathogenic and resistant strains. The designed antibiotics show antibacterial activity superior to that of neomycin B against pathogenic and resistant bacterial strains.

  DOI：

  10.1021/ol035213i

文献信息

• Bifunctional antibiotics for targeting rRNA and resistance-causing enzymes
  申请人：Baasov Timor

  公开号：US20050004052A1

  公开（公告）日：2005-01-06

  A novel group of aminoglycosides which share some structural features of currently available aminoglycosides with regard to the backbone, while also having significant structural differences. The similarity enables these aminoglycosides to be highly potent and effective antibiotics, while the significant differences enable these aminoglycosides to reduce or even block antibiotic resistance.

  一种新型氨基糖苷类药物，与目前已有的氨基糖苷类药物在骨架方面具有一些结构特征，同时又具有显著的结构差异。这种相似性使得这些氨基糖苷类药物具有很高的抗菌作用和有效性，而显著的差异使得这些氨基糖苷类药物能够减少甚至阻止抗生素耐药性的发展。
• An expeditious route to the synthesis of kelampayosides A and B
  作者：Howard I. Duynstee、Martijn C. de Koning、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/s0040-4020(99)00527-x

  日期：1999.8

  Chemoselective NIS/ cat. TfOH-mediated glycosylation of ethyl2,3,4-tri-O-benzoyl-1-thio-β-d-glucopyranoside (13) with ethyl2,3-di-O-acetyl-5-O-benzyl-1-thio-αβ-d-erythro-apiofuranoside (4a) gave dimer14 in an excellent yield. BF3•Et2O-catalysed condensation of the α-trichloroacetimidate31, accessible in two steps from14, with 3,4,5-trimethoxyphenol gave β-linked derivative32 followed by deprotection

  化学选择性NIS /猫。TfOH介导的乙基2,3,4-三-O-苯甲酰基-1-硫代-β-d-吡喃葡萄糖苷（13）与乙基2,3-二-O-乙酰基-5-O-苄基-1-硫代-的糖基化作用αβ-d-赤型-呋喃呋喃糖苷（4a）以优异的产率得到二聚体14。BF 3 •Et 2 O催化的α-三氯乙酰亚胺酸酯31的缩合反应（从14步可分两个步骤进行）与3,4,5-三甲氧基苯酚生成β-连接的衍生物32，然后脱保护得到KelampayosideA。保护基的操作为32和所得的后续caffeoylation 36接着进行脱保护，得到Kelampayoside B.图选项
• Bifunctional antibiotics for targeting rRNA and resistance-causing enzymes and for inhibition of anthrax lethal factor
  申请人：Baasov Timor

  公开号：US20050148522A1

  公开（公告）日：2005-07-07

  A novel group of aminoglycosides which share some structural features of currently available aminoglycosides with regard to the backbone, while also having significant structural differences, is disclosed. The similarity enables these aminoglycosides to be highly potent and effective antibiotics, while the significant differences enable these aminoglycosides to reduce or even block antibiotic resistance. The aminoglycosides of the present invention are suitable for inhibition of antrax lethal factor, hence are suitable for use as a cure for anthrax.

  本研究揭示了一组新型氨基糖苷类药物，它们在骨架方面与现有的氨基糖苷类药物具有一些相同的结构特征，同时在结构上也有显著差异。相似性使这些氨基糖苷类药物成为强效和有效的抗生素，而显著的差异则使这些氨基糖苷类药物能够减少甚至阻止抗生素耐药性的产生。本发明的氨基糖苷类药物适用于抑制抗炭疽致死因子，因此适用于治疗炭疽。
• BIFUNCTIONAL ANTIBIOTICS FOR TARGETING RRNA AND RESISTANCE CAUSING ENZYMES AND FOR INHIBITION OF ANTHRAX LETHAL FACTOR
  申请人：TECHNION RESEARCH AND DEVELOPMENT FOUNDATION, LTD.

  公开号：EP1789429A2

  公开（公告）日：2007-05-30
• US7635685B2
  申请人：——

  公开号：US7635685B2

  公开（公告）日：2009-12-22