Methyl 4-deoxy-4-fluoro-6-O-trityl-α-D-galactopyranoside | 87586-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Methyl 4-deoxy-4-fluoro-6-O-trityl-α-D-galactopyranoside
• 英文别名: methyl 4-deoxy-4-fluoro-6-O-trityl-α-D-glucopyranoside；methyl 4-deoxy-4-fluoro-6-trityl-α-D-galactopyranoside；methyl 4-deoxy-4-fluoro-6-O-trityl-α-D-glucopyranose；methyl 4-fluoro-4-deoxy-6-O-trityl-galactopyranoside
• CAS: 87586-00-3
• 化学式: C₂₆H₂₇FO₅
• 分子量: 438.496
• InChiKey: HLTZCKHEKHGOJO-MQZWXTIWSA-N

物化性质

• 沸点：
  572.8±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Methyl 4-deoxy-4-fluoro-6-O-trityl-α-D-galactopyranoside 在 盐酸 、 对甲苯磺酸 、 sodium sulfate 作用下， 以 乙醇 、 氯仿 、 丙酮 为溶剂， 反应 50.0h， 生成 1,2:4,5-di-O-isopropylidene-3-deoxy-3-fluoro-L-fucitol
  参考文献：
  名称：

  Chemoenzymatic synthesis of 3-deoxy-3-fluoro-l-fucose and its enzymatic incorporation into glycoconjugates

  摘要：

  使用d-到l-糖转化策略合成3-去氧-3-氟-l-葡萄糖，进行酶催化活化和糖基化。

  DOI：

  10.1039/d0cc02209h
• 作为产物：
  描述：

  三苯基氯甲烷 在 吡啶 、 二乙胺基三氟化硫 作用下， 以 neat (no solvent) 为溶剂， 反应 51.5h， 生成 Methyl 4-deoxy-4-fluoro-6-O-trityl-α-D-galactopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of 3-deoxy-3-fluoro-l-fucose and its enzymatic incorporation into glycoconjugates

  摘要：

  使用d-到l-糖转化策略合成3-去氧-3-氟-l-葡萄糖，进行酶催化活化和糖基化。

  DOI：

  10.1039/d0cc02209h

文献信息

• Selectively Deoxyfluorinated <i>N</i> ‐Acetyllactosamine Analogues as ¹⁹ F NMR Probes to Study Carbohydrate‐Galectin Interactions
  作者：Martin Kurfiřt、Martin Dračínský、Lucie Červenková Šťastná、Petra Cuřínová、Vojtěch Hamala、Michaela Hovorková、Pavla Bojarová、Jindřich Karban

  DOI：10.1002/chem.202101752

  日期：2021.9.9

  synthesized a complete series of six mono-deoxyfluorinated analogues of LacNAc, in which each hydroxyl has been selectively replaced by fluorine while the anomeric position has been protected as methyl β-glycoside. Initial evaluation of their binding to human galectin-1 and -3 by ELISA and 19F NMR T2-filter revealed that deoxyfluorination at C3, C4′ and C6′ completely abolished binding to galectin-1 but

  半乳糖凝集素是广泛表达的半乳糖结合凝集素，例如在免疫调节、转移扩散和病原体识别中暗示。N-乙酰乳糖胺（Galβ1-4GlcNAc、LacNAc）及其寡聚或糖基化形式是半乳糖凝集素的天然配体。为了探测半乳糖凝集素的底物特异性和结合模式，我们合成了完整系列的六种 LacNAc 单脱氧氟化类似物，其中每个羟基都被氟选择性取代，而异头位置被保护为甲基β-糖苷。通过 ELISA 和19 F NMR T 2初步评估它们与人半乳糖凝集素-1 和 -3 的结合-filter 显示 C3、C4' 和 C6' 处的脱氧氟化完全消除了与 galectin-1 的结合，但仍可检测到与 galectin-3 的非常弱的结合。此外，C2' 的脱氧氟化导致对 galectin-1 的结合亲和力增加了大约 8 倍，而与 galectin-3 的结合基本上不受影响。亲脂性测量表明，与 GlcNAc 部分的脱氧氟化作用相比，Gal
• Stereo- and regio-selectivity of diethylaminosulfur trifluoride as a fluorinating reagent for methyl glycosides
  作者：Chandrasiri W. Somawardhana、Eric G. Brunngraber

  DOI：10.1016/0008-6215(83)84005-1

  日期：1983.9

  Methyl glycopyranosides reacted with diethylaminosulfur trifluoride (DAST) in the absence of solvent to yield methyl dideoxy-difluoro and deoxy-fluoro glycopyranosides. Methyl alpha-D-glycopyranosides produced 6-deoxy-6-fluoro- and 4,6-dideoxy-4,6-difluoro derivatives with Walden inversion at C-4. Methyl beta-D-glucopyranoside also produced a 3,6-dideoxy-3,6-difluoro derivative, with Walden inversion

  在没有溶剂的情况下，甲基吡喃葡萄糖苷与二乙基氨基三氟化硫（DAST）反应，生成甲基双脱氧二氟和脱氧氟吡喃葡萄糖苷。甲基α-D-吡喃葡萄糖苷产生6-脱氧-6-氟-和4,6-二脱氧-4,6-二氟衍生物，在C-4处有沃尔登反型。甲基β-D-吡喃葡萄糖苷也产生了3,6-dideoxy-3,6-difluoro衍生物，在C-3处有Walden倒置。甲基6-O-三苯甲基-α-D-吡喃葡萄糖苷与DAST反应生成相应的4-脱氧-4-氟吡喃半乳糖苷衍生物。
• 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 UDP-4-deoxy-4-fluoroglucose and UDP-4-deoxy-4-fluorogalactose and their Interactions with Enzymes of Nucleotide Sugar Metabolism
  作者：Marie-Christine Chapeau、Perry A. Frey

  DOI：10.1021/jo00102a024

  日期：1994.11

  Fluorinated carbohydrates can be used as probes of enzymatic active sites. We report the synthesis of 4-deoxy-4-fluoro-alpha-D-galactose-1-phosphate and the substrate analogues of UDP-galactose, UDP-4-deoxy-4-fluoro-alpha-D-galactose (UDP-FGal), and of UDP-glucose, UDP-4-deoxy-4-fluoro-alpha-D-glucose (UDP-FGlc), which may be useful in analyzing the binding properties of enzymes that utilize nucleotide sugars as substrates. As a first step in this study, we determine the kinetic and inhibition parameters for UDP-FGal and UDP-FGlc interacting with UDP-glucose dehydrogenase and UDP-galactose 4-epimerase. UDP-FGlc is a substrate for bovine liver UDP-glucose dehydrogenase: K-m = 30.2 +/- 4.5 mu M slightly higher than the value 9.6 +/- 0.7 mu M for UDP-glucose, and V-mUDP-FGlc = 046V (mUDP-Glc). UDP-FGal is not a substrate for UDP-glucose dehydrogenase but is a competitive inhibitor with respect to UDP-glucose (K-i = 19.9 +/- 6.6 mu M). These analogs also bind to UDP-galactose 4-epimerase from E. coli with dissociation constants K-d of 1.4 and 1.1 mM for UDP-FGlc and UDP-FGal, respectively.