2-deoxy-2-trifluoroacetamido-α-D-glucopyranose | 38567-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2-trifluoroacetamido-α-D-glucopyranose
• 英文别名: N-trifluoroacetylglucosamine；N-trifluoroacetyl-α-D-glucosamine；2-deoxy-2-(trifluoroacetyl)amino-D-glucopyranose；2-Deoxy-2-trifluoracetamido-α-D-glucose；2-deoxy-2-(2,2,2-trifluoroacetamido)-α-D-glucopyranose；2-Desoxy-2-trifluoracetamido-α-D-glucopyranose；2,2,2-trifluoro-N-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 38567-96-3
• 化学式: C₈H₁₂F₃NO₆
• 分子量: 275.182
• InChiKey: ZXNYUXIMAXVSFN-UKFBFLRUSA-N

物化性质

• 熔点：
  197-199 °C
• 沸点：
  514.6±50.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-trifluoroacetamido-α-D-glucopyranose 、 油醇 在 silica gel supported sulfuric acid 作用下， 反应 0.33h， 以29%的产率得到oleyl N-trifluoroacetyl-α-D-glucosaminide
  参考文献：
  名称：

  USE OF SULPHATED GLYCOLIPIDS AS PROMOTERS OF NEURITIC GROWTH AND MYELINATION AND INHIBITORS OF THE PROLIFERATION OF ASTROGLIA AND MICROGLIA

  摘要：

  本发明涉及一种具有公式I的化合物的使用，其中R1是含有一个或多个双碳-碳键的C5-C25烯基团，R2独立地选自甲基和氟甲基组成的组，R3和/或R4是SO3M基团，其中M选自由氢、碱金属、铵和季铵组成的组，另一个是氢或酰基，用于制备用于治疗中枢神经系统障碍的药物，该障碍选自由中枢神经系统创伤引起的损伤、脱髓鞘疾病、神经炎症疾病和由低水平脑源性神经营养因子（BDNF）引起的精神障碍。本发明还涉及具有公式I的化合物，制备所述化合物的方法以及包含该化合物的组合物。

  公开号：

  EP2871183A1
• 作为产物：
  描述：

  在 水 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-deoxy-2-trifluoroacetamido-α-D-glucopyranose 、 2-deoxy-2-(2,2,2-trifluoroacetamido)-β-D-glucopyranose
  参考文献：
  名称：

  通过全氟化酸酐对仲酰胺进行一般和化学选择性的N-酰化

  摘要：

  直接途径：报道了仲酰胺经N-酰化成全氟化类似物的可能性，随后可能转化为正酰胺（见方案）。该反应在多种官能团的存在下发生，这些官能团对经典的N-酰化反应所需的水解条件不利。

  DOI：

  10.1002/anie.200906055

文献信息

• Tailored Design and Synthesis of Heparan Sulfate Oligosaccharide Analogues Using Sequential One-Pot Multienzyme Systems
  作者：Yi Chen、Yanhong Li、Hai Yu、Go Sugiarto、Vireak Thon、Joel Hwang、Li Ding、Liana Hie、Xi Chen

  DOI：10.1002/anie.201305667

  日期：2013.11.4

  Heparan sulfate analogues: Highly efficient one‐pot multienzyme (OPME) chemoenzymatic systems for the activation and transfer of N‐acetylglucosamine (GlcNAc) and glucuronic acid (GlcA) have been developed. They were applied to the sequential tailored synthesis of N‐sulfated analogues of heparan sulfate oligosaccharides, which could be potential therapeutics.

  硫酸乙酰肝素类似物：已经开发出高效的一锅多酶（OPME）化学酶系统，用于激活和转移N-乙酰氨基葡萄糖（GlcNAc）和葡萄糖醛酸（GlcA）。它们被应用于硫酸乙酰肝素寡糖的N-硫酸化类似物的连续定制合成，这可能是潜在的治疗方法。
• Efficient Synthesis of Azido Sugars Using Fluorosulfuryl Azide Diazotransfer Reagent**
  作者：Joshua M. Kofsky、Gour C. Daskhan、Matthew S. Macauley、Chantelle J. Capicciotti

  DOI：10.1002/ejoc.202200108

  日期：2022.8.5

  An operationally simple protocol for diazotransfer on amine-containing carbohydrates has been developed. This high-yielding reaction can be conducted under ambient conditions. Reaction completion is indicated by the colour change of the Cu(II) catalyst. The utility of this protocol in chemical glycosylation has been demonstrated through the preparation of azide-containing glycosyl donors with orthogonal

  已开发出一种操作简单的含胺碳水化合物重氮转移方案。这种高产反应可以在环境条件下进行。反应完成由 Cu(II) 催化剂的颜色变化指示。该协议在化学糖基化中的效用已通过制备具有正交保护基团的含叠氮化物糖基供体得到证明。
• Novel sugar bola-amphiphiles with a pseudo macrocyclic structure
  作者：Jean-Noel Bertho、Annie Coué、David F. Ewing、John W. Goodby、Phillipe Letellier、Grahame Mackenzie、Daniel Plusquellec

  DOI：10.1016/s0008-6215(97)00071-2

  日期：1997.5

  Novel bola-amphiphilic compounds have been synthesised with D-glucose or D-galactose moieties as polar head groups. The sugar groups are coupled to the hydrophobic bridge, a chain of ten or twelve methylene groups, by an amide function at the C-2 site (2-alkylamido-2-deoxy-D-glucose derivative) or a glycuronamido function at the C-6 site. The former series is glycosylated with a cinnamyl group and the latter with octyl or decyl groups to afford pseudo macrocyclic compounds. (C) 1997 Elsevier Science Ltd.
• USE OF SULPHATED GLYCOLIPIDS AS PROMOTERS OF NEURITIC GROWTH, MYELINATION AND INHIBITING THE PROLIFERATION OF ASTROGLIA AND MICROGLIA
  申请人：CONSEJO SUPERIOR DE INVESTIGACIONES CIENTIFICAS (CSIC)

  公开号：US20150307539A1

  公开（公告）日：2015-10-29

  A compound having formula I, in which R 1 is an alkenyl group C 5 -C 25 containing one or more double carbon-carbon bonds, R 2 is selected independently from the group consisting of methyl and fluorinated methyl, and R 3 and/or R 4 is a SO 3 M group, in which M is selected from the group consisting of hydrogen, alkali metal, ammonium and quaternary amine, the other being hydrogen or acyl is provided. The compound can be used for the production of a drug for the treatment of central nervous system disorders selected from the group consisting of lesions caused by CNS trauma, demyelinating diseases, neuro-inflammatory diseases and mental disorders caused a low level of BDNF.
• USE OF SULPHATED GLYCOLIPIDS AS PROMOTERS OF NEURITIC GROWTH AND MYELINATION AND INHIBITORS OF THE PROLIFERATION OF ASTROGLIA AND MICROGLIA
  申请人：Consejo Superior De Investigaciones Científicas (CSIC)

  公开号：EP2871183A1

  公开（公告）日：2015-05-13

  The invention relates to the use of a compound having formula I, in which R1 is an alkenyl group C5-C25 containing one or more double carbon-carbon bonds, R2 is selected independently from the group consisting of methyl and fluorinated methyl, and R3 and/or R4 is a SO3M group, in which M is selected from the group consisting of hydrogen, alkali metal, ammonium and quaternary amine, the other being hydrogen or acyl, for the production of a drug for the treatment of central nervous system disorders selected from the group consisting of lesions caused by CNS trauma, demyelinating diseases, neuro-inflammatory diseases and mental disorders caused a low level of BDNF. The invention also relates to compounds having formula I, to methods for producing said compounds and to compositions containing same.

  本发明涉及一种具有公式I的化合物的使用，其中R1是含有一个或多个双碳-碳键的C5-C25烯基团，R2独立地选自甲基和氟甲基组成的组，R3和/或R4是SO3M基团，其中M选自由氢、碱金属、铵和季铵组成的组，另一个是氢或酰基，用于制备用于治疗中枢神经系统障碍的药物，该障碍选自由中枢神经系统创伤引起的损伤、脱髓鞘疾病、神经炎症疾病和由低水平脑源性神经营养因子（BDNF）引起的精神障碍。本发明还涉及具有公式I的化合物，制备所述化合物的方法以及包含该化合物的组合物。