1,2,3,4-四-O-乙酰基-6-脱氧-6-氟-D-吡喃葡萄糖 | 31337-78-7

• 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
• 中文名称: 1,2,3,4-四-O-乙酰基-6-脱氧-6-氟-D-吡喃葡萄糖
• 英文名称: 1,2,3,4-Tetra-O-acetyl-6-deoxy-6-fluoro-D-glucofuranose
• 英文别名: 6-deoxy-6-fluoro-1,2,3,4-tetra-O-acetyl-D-glucopyranose；[(2S,3S,4S,5R)-4,5,6-triacetyloxy-2-(fluoromethyl)oxan-3-yl] acetate
• CAS: 31337-78-7
• 化学式: C₁₄H₁₉FO₉
• 分子量: 350.298
• InChiKey: NGYYXVXMDLMRLI-RQICVUQASA-N

物化性质

• 沸点：
  387.8±42.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  10

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  1,2,3,4-四-O-乙酰基-6-脱氧-6-氟-D-吡喃葡萄糖 在 氢溴酸 、 溶剂黄146 作用下， 反应 1.0h， 以95%的产率得到2,3,4-Tri-O-acetyl-6-deoxy-6-fluoro-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  Synthesis of 6-fluoro-d-olivose (2,6-dideoxy-6-fluoro-d-arabino-hexopyranose)

  摘要：

  An efficient synthesis of 6-fluoro-D-olivose 5 (2,6-dideoxy-6-fluoro-D-arabino-hexopyranose starting from D-glucose is reported. Key features of the synthesis involve the early introduction of the fluorine atom at C-6 and the Fischer reductive elimination as a strategy to achieve C-2 deoxygenation. The route, the first to this compound, is efficient providing gramme quantities of 5 for biotransformation studies. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(98)00220-6
• 作为产物：
  描述：

  乙酸酐 、 methyl 6-deoxy-6-fluoro-α-D-glucopyranoside 在 硫酸 作用下， 生成 1,2,3,4-四-O-乙酰基-6-脱氧-6-氟-D-吡喃葡萄糖
  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 α-Deoxymono and Difluorohexopyranosyl 1-Phosphates and Kinetic Evaluation with Thymidylyl- and Guanidylyltransferases
  作者：Jian-She Zhu、Nicole E. McCormick、Shannon C. Timmons、David L. Jakeman

  DOI：10.1021/acs.joc.6b01485

  日期：2016.10.7

  monofluoro substitution at C-2, C-4, and C-6 and difluoro substitution at C-2 within two orders of magnitude. In contrast, the kinetic analysis of GDP-ManPP was only possible with three out of eight analogues. The pKa2 values of analogues (1–3) were determined by proton decoupled 31P and 19F NMR titration experiments. Counterintuitively, the axial fluoro substituent in 3 did not change chemical shift upon

  已经合成了八个氟化的等排α - d-吡喃葡萄糖基1-磷酸酯（Glc 1P）类似物。胸腺嘧啶转移酶Cps2L和胍基转移酶GDP-ManPP与这些类似物的滥交调查显示，除1,6-二磷酸6以外，所有这些均被任一酶所接受。使用连续偶联测定法确定这些类似物的动力学参数。这些数据证明了Cps2L的广泛底物滥交，k cat / K mC-2，C-4和C-6处的单氟取代和C-2处的二氟取代在两个数量级内变化。相反，只有八分之三的类似物才能对GDP-ManPP进行动力学分析。在p ķ一个2个类似物的值（1 - 3）通过质子去耦测定31 P和19个F NMR滴定实验。与直觉相反，在3中的轴向氟取代基在滴定时没有改变化学位移，并且与单氟类似物相比，二氟类似物的酸度没有显着增加。在所有五种底物之间均未观察到强烈的布朗斯台德线性自由能相关性（1 –3，Glc 1P和Man 1P）用于任一酶催化的反应。但是，在选定的
• Synthesis of glycyrrhizin analogues containing fluorinated β(1→2)-linked disaccharides
  作者：Naohiko Morishima、Yoko Mori

  DOI：10.1016/s0968-0896(96)00169-1

  日期：1996.11

  For studies on the recognition mechanisms for Glycyrrhizin-induced biological activities, seven Glycyrrhizin analogues with 3'-,4'-,6'-,3-, and 4-fluorinated 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoses (1-5) and 3- and 4-fluorinated 2-O-beta-D-glucopyranuronosyl-beta-D-glucopyranoses (6 and 7) were synthesized through a stepwise glycosylation procedure. 1,2-Di-O-acetyl-4,6-di-0-benzyl-3-deoxy-3-fluoro- (13) and 1,2-di-O-acetyl-3,6-di-O-benzyl-4-deoxy-4-fluoro-D-glucopyranose (14) were employed for the first beta-glycosylation of methyl glycyrrhetate, promoted with trimethylsilyl trifluoromethanesulfonate. Copyright (C) 1996 Elsevier Science Ltd
• Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin
  作者：Bryan Elchert、Jie Li、Jinhua Wang、Yu Hui、Ravi Rai、Roger Ptak、Priscilla Ward、Jon Y. Takemoto、Mekki Bensaci、Cheng-Wei Tom Chang

  DOI：10.1021/jo035290r

  日期：2004.3.1

  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.
• Synthesis of 6-fluoro-d-olivose (2,6-dideoxy-6-fluoro-d-arabino-hexopyranose)
  作者：Jens Nieschalk、David O'Hagan

  DOI：10.1016/s0022-1139(98)00220-6

  日期：1998.9

  An efficient synthesis of 6-fluoro-D-olivose 5 (2,6-dideoxy-6-fluoro-D-arabino-hexopyranose starting from D-glucose is reported. Key features of the synthesis involve the early introduction of the fluorine atom at C-6 and the Fischer reductive elimination as a strategy to achieve C-2 deoxygenation. The route, the first to this compound, is efficient providing gramme quantities of 5 for biotransformation studies. (C) 1998 Elsevier Science S.A. All rights reserved.