methyl 3-deoxy-3-fluoro-α-D-glucopyranoside | 33941-74-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-deoxy-3-fluoro-α-D-glucopyranoside
• 英文别名: (2R,3R,4S,5S,6S)-4-fluoro-2-(hydroxymethyl)-6-methoxyoxane-3,5-diol
• CAS: 33941-74-1
• 化学式: C₇H₁₃FO₅
• 分子量: 196.176
• InChiKey: CCAXOPTXMDCKMO-BIVRFLNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-deoxy-3-fluoro-α-D-glucopyranoside 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 生成 methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-fluoro-α-D-glucopyranoside
  参考文献：
  名称：

  Regioselectivity of Reductive Cleavage of Methyl 4,6-O-Benzylidene-3-deoxyhexopyranosides Containing Fluorine at the 2- or 3-Position with LiAlH₄–AlCl₃

  摘要：

  甲基 3-脱氧-β-d-阿拉伯苷、3-脱氧-α-d-核苷和 2-O-苄基-3-脱氧-α-d-核六吡喃糖苷的 4,6-O-亚苄基衍生物与 LiAlH4 和 AlCl3 按 4 : 4 的摩尔比进行还原开环反应，得到 4-和 6-O-苄基衍生物，比例为 7 : 3。甲基 4,6-O-亚苄基-2,3-二脱氧-2-氟-α-d-阿拉伯和 β-d-核吡喃糖苷与甲基 2-O-苄基-4,6-O-亚苄基-3-脱氧-3-氟-α-d-葡糖和 β-d-全吡喃糖苷反应的产物比分别为 3:2、2:3、1:1 和 3:7。然而，当试剂的摩尔比为 2 : 4 时，上述所有 4,6-O-亚苄基衍生物反应的产物比约为 4 : 1。本文讨论了 C-2 或 C-3 上的氟以及 LiAlH4 和 AlCl3 的摩尔比对 4,6-O-亚苄基吡喃己糖苷还原裂解反应的区域选择性的影响。

  DOI：

  10.1246/bcsj.66.2061
• 作为产物：
  描述：

  3-deoxy-3-fluoro-1,2:5,6-di-O-isopropylidene-α-d-glucofuranose 在 乙酰氯 作用下， 以 甲醇 为溶剂， 以33.333%的产率得到
  参考文献：
  名称：

  新型氟化膦酰基 C-糖苷（3-脱氧-3-氟-β-d-吡喃葡萄糖基）甲基膦酸酯的合成，它是 β-磷酸葡萄糖变位酶的潜在抑制剂

  摘要：

  β-磷酸葡萄糖变位酶 (βPGM) 通过两步过程催化 β-葡萄糖 1-磷酸 (βG1P) 转化为葡萄糖-6-磷酸 (G6P)，这是细胞能量的通用来源。由底物类似物和金属氟化物（MgF 3 -和 AlF 4 - ）形成的过渡态类似物（TSA）复合物能够独立分析每个酶促步骤。含有氟的新型底物类似物提供了使用19 F NMR 光谱来探究酶机制的机会。本文公开了新型氟化膦酰基C-糖苷(3-脱氧-3-氟-β- d-吡喃葡萄糖基)甲基膦酸酯( 1 )的合成，分12步进行(总收率0.85％)。采用四阶段合成策略，包括：1）向单糖添加氟，2）选择性异头去保护，3）异头中心磷酸化，以及4）整体去保护。 βPGM 和1的分析将在适当的时候报告。

  DOI：

  10.1016/j.carres.2023.108979

文献信息

• Molecular recognition in the P2Y14 receptor: Probing the structurally permissive terminal sugar moiety of uridine-5′-diphosphoglucose
  作者：Hyojin Ko、Arijit Das、Rhonda L. Carter、Ingrid P. Fricks、Yixing Zhou、Andrei A. Ivanov、Artem Melman、Bhalchandra V. Joshi、Pavol Kováč、Jan Hajduch、Kenneth L. Kirk、T. Kendall Harden、Kenneth A. Jacobson

  DOI：10.1016/j.bmc.2009.05.024

  日期：2009.7

  substitution by chain extension through an amide linkage. Functionalized congeners containing terminal 2-acylaminoethylamides prepared by this strategy retained P2Y14 activity, and molecular modeling predicted close proximity of this chain to the second extracellular loop of the receptor. In addition, replacement of glucose with other sugars did not diminish P2Y14 potency. For example, the [5′′]ribose derivative

  P2Y 14受体是一种核苷酸信号蛋白，由尿苷-5'-二磷酸葡萄糖1和其他尿嘧啶核苷酸激活。我们已经确定1的葡萄糖部分是设计该 P2Y 14激动剂类似物的最结构允许区域。例如，尿苷-5'-二磷酸葡萄糖醛酸的羧酸酯基团被证明适用于通过酰胺键进行链延伸的灵活取代。通过该策略制备的含有末端 2-酰基氨基乙基酰胺的功能化同源物保留了 P2Y 14活性，分子模型预测该链与受体的第二个细胞外环非常接近。此外，用其他糖替代葡萄糖不会降低 P2Y 14效力。例如，[5'']核糖衍生物的EC 50为0.24 μM。的葡萄糖部分的选择性monofluorination指示用于2'角色' -和6'' -的羟基1受体识别。β-葡萄糖苷的效力比天然 α-异构体低两倍，但 1''-氧的亚甲基替代消除了活性。用环戊基或刚性双环 [3.1.0] 己烷基团取代核糖环系统消除了活性。Uridine-5'-diphosphoglucose
• A synthetic study of methyl 3-deoxy-3-fluoro-α-d-glucopyranosides from methyl 2,3-anhydro-α-d-allopyranosides, and synthesis of 3′-deoxy-3′-fluorokanamycin A and 3′-chloro-3′-deoxykanamycin A
  作者：Eijiro Umemura、Tsutomu Tsuchiya、Yoshihiko Kobayashi、Koichi Tanaka

  DOI：10.1016/0008-6215(92)84101-w

  日期：1992.2

  utilized to measure the effects of solvation and hydrogen bonding relative to the C-4 and C-6 substituents. By application of this reaction, 3′-deoxy-3′-fluorokanamycin A has been prepared by treatment of a 2′,3′-anhydro-3′-epikanamycin A derivative ( 35 ) with KHF 2 . 3′-Chloro-3′-deoxykanamycin A was also prepared.

  摘要在环氧乙烷-1，2-二醇中，4，6-二取代的2，3-脱水-α-d-吡喃果糖苷与氟化氢钾（KHF 2）反应通过环氧乙烷环开环得到相应的2-脱氧-2-氟代-α-d-氨基和3-脱氧-3-氟代-α-d-葡萄糖基吡喃糖基衍生物，后者总是占优势。通过分子力学研究了C-4和C-6处取代基对d-葡萄糖-d-altro（r）的影响，并积极利用实验值和计算值r的差异来衡量效果相对于C-4和C-6取代基的溶剂化和氢键的关系。通过应用该反应，通过用KHF 2处理2′，3′-脱水-3′-表卡那霉素A衍生物（35），制备了3′-脱氧-3′-氟卡那霉素A。还制备了3'-氯-3'-脱氧卡那霉素A。
• 2'-DEOXY-2'-FLUOROCOFORMYCIN AND STEREOISOMERS THEREOF
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP0643069A1

  公开（公告）日：1995-03-15

  2'-Deoxy-2'-fluorocoformycin and 2'-deoxy-8-epi-2'-fluorocoformycin have now been synthesized by a multistage reaction via 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α- and -β-D-ribofuranosyl bromide. Also 2'-deoxy-2'-epi-2'-fluorocoformycin and 2'-deoxy-8,2'-diepi-2'-fluorocoformycin have been synthesized from 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranosyl bromide by a multistage reaction. These four 2'-fluorocoformycin derivatives are novel compounds and have a potent enzyme inhibiting activity against adenosine deaminase. In particular, they are useful for treating acute lymphocytic leukemia in virtue of the above activity. Other novel compounds also obtained include various intermediates useful for the synthesis of the above derivatives.

  2'-Deoxy-2'-fluorocoformycin 和 2'-deoxy-8-epi-2'-fluorocoformycin 现已通过 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α- 和 -β-D-ribofuranosyl bromide 的多级反应合成。此外，3,5-二-O-苯甲酰基-2-脱氧-2-氟-α-D-阿拉伯呋喃糖基溴化物通过多级反应合成了 2'-deoxy-2'-epi-2'-fluorocoformycin 和 2'-deoxy-8,2'-diepi-2'-fluorocoformycin 。这四种 2'-氟甲酰霉素衍生物是新型化合物，对腺苷脱氨酶具有强效的酶抑制活性。由于具有上述活性，它们特别适用于治疗急性淋巴细胞白血病。此外，还获得了其他新型化合物，包括用于合成上述衍生物的各种中间体。
• A process for the preparation of 2'-deoxy-2'-halocoformycins or stereoisomers thereof
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP0794194B1

  公开（公告）日：2001-12-12
• Method for Optimizing Post-Translational Modifications on Recombinant Proteins
  申请人：LESZCYNIECKA Magdalena

  公开号：US20160340706A1

  公开（公告）日：2016-11-24

  A method for optimizing post-translational modifications of recombinant proteins expressed in living cells is described. More particularly, a method for modulation of host proteins in living cells that control PTMs on recombinant proteins is described that has particularly useful applications in developing manufacturing process changes or in biosimilar development. The goal of this modulation is to produce a recipe for production of a recombinant protein in the new process or in the biosimilar that will produce a targeted PTM profile in the resulting protein product. In the method one or more modulators are selected, as from a modulator library, which affect the activity of host proteins. These modulators are added to media during production such that the resulting product matches the PTMs of the reference product. The ideal set of modulators and their concentrations are identified through a unique iterative process and the combined modulators and their concentrations constitute a recipe for growth media for the production of said recombinant protein. The methodology to obtain such a recipe described herein may then be used in many applications, such as optimizing new batches of recombinant protein drugs, developing biosimilar or bio-better drugs.