己基-2,3,4,6-四-氧-乙酰基-β-D-吡喃葡萄糖苷 | 172945-26-5

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 己基-2,3,4,6-四-氧-乙酰基-β-D-吡喃葡萄糖苷
• 中文别名: 己基-2,3,4,6-四-氧-乙酰基-Β-D-吡喃葡萄糖苷
• 英文名称: hexyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: Hexyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-hexoxyoxan-2-yl]methyl acetate
• CAS: 172945-26-5
• 化学式: C₂₀H₃₃NO₉
• 分子量: 431.483
• InChiKey: RZSSLCQNNAGTQY-LASHMREHSA-N

物化性质

• 沸点：
  555.7±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  己基-2,3,4,6-四-氧-乙酰基-β-D-吡喃葡萄糖苷 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 己基-2-乙酰氨基-2-脱氧-β-D-吡喃葡糖苷
  参考文献：
  名称：

  SLe x模拟物的合成：潜在的E-选择素结合拮抗剂

  摘要：

  4,7,8,9-四-O-乙酰基-N-乙酰基-2- O- [3-（甲硫基甲氧基）丙基]-α-D-神经氨酸的碘鎓离子辅助缩合（15）与己基2 -乙酰氨基-6- O-苄基-3- O-（三-O-苄基-α-L-呋喃核糖基）-2-脱氧-β-D-吡喃葡萄糖苷（12），在脱保护后提供SLe x模拟物3。通过将15与2-乙酰氨基-3-己基-3- O-苯甲酰基-6- O-苄基-2-脱氧-β-D-吡喃葡萄糖苷（15）偶联，以类似的方式获得了非岩藻糖基化衍生物2（8）。

  DOI：

  10.1002/recl.19951140905
• 作为产物：
  描述：

  2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 在 1H-1,2,4-三唑 、 三氟甲磺酸三甲基硅酯 、 双氧水 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 己基-2,3,4,6-四-氧-乙酰基-β-D-吡喃葡萄糖苷
  参考文献：
  名称：

  New α-selective thermal glycosylation of acetyl-protected 2-acetamido-2-deoxy-β-d-glucopyranosyl diphenylphosphinate

  摘要：

  This paper describes new alpha-selective thermal glycosylation using acetyl-protected 2-acetamido-2-deoxy-beta-D-glucopyranosyl diphenylphosphinate (4) as a glycosyl donor. When the glycosylation of 4 with 1-hexanol was carried out under Various conditions, the conditions using trimethylsilyl trifluoromethanesulfonate as a promoter in nitromethane at reflux temperature were most suitable for the formation of the alpha anomer. The glycosylation of 4 with the other common alcohols gave corresponding alpha-glycosides in relatively high yields under the conditions. When cholesterol, a very steric hindered alcohol, was used as a glycosyl acceptor, alpha-glycoside was also produced predominantly. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00069-0

文献信息

• Synthesis of a SLex mimic: A potential E-selectin binding antagonist
  作者：B. M. Heskamp、G. H. Veeneman、G. A. van der Marel、C. A. A. van Boeckel、J. H. van Boom

  DOI：10.1002/recl.19951140905

  日期：——

  yl-2-O-[3- (methylthiomethoxy)propyl]-α-D-neuraminate (15) with hexyl 2-acetamido-6-O-benzyl-3-O-(tri-O- benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside (12) furnished, after deprotection, SLex mimic 3. The non-fucosylated derivative 2 was obtained in a similar fashion by the coupling of 15 with hexyl 2-acetamido-3-O-benzoyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside (8).

  4,7,8,9-四-O-乙酰基-N-乙酰基-2- O- [3-（甲硫基甲氧基）丙基]-α-D-神经氨酸的碘鎓离子辅助缩合（15）与己基2 -乙酰氨基-6- O-苄基-3- O-（三-O-苄基-α-L-呋喃核糖基）-2-脱氧-β-D-吡喃葡萄糖苷（12），在脱保护后提供SLe x模拟物3。通过将15与2-乙酰氨基-3-己基-3- O-苯甲酰基-6- O-苄基-2-脱氧-β-D-吡喃葡萄糖苷（15）偶联，以类似的方式获得了非岩藻糖基化衍生物2（8）。
• Compositions and methods for treatment of inflammatory disorders
  申请人：THE JOHNS HOPKINS UNIVERSITY

  公开号：US10668092B2

  公开（公告）日：2020-06-02

  The present invention relates to methods of treating infectious, inflammatory and post-traumatic disorders by administering various compounds newly discovered to have TLR4 inhibitory activity. In addition to methods of treatment, the present invention further provides for pharmaceutical compositions comprising said compounds, together with a suitable pharmaceutical carrier.

  本发明涉及通过施用新发现的具有 TLR4 抑制活性的各种化合物来治疗感染性、炎症性和创伤后疾病的方法。除治疗方法外，本发明还进一步提供了药物组合物，其中包含上述化合物以及合适的药物载体。
• Alkylating agents from sugars. Alkyl hexopyranoside derivatives as carrier systems for chlorambucil
  作者：Fernando Iglesias-Guerra、José I Candela、Juan Bautista、Felipe Alcudia、José M Vega-Pérez

  DOI：10.1016/s0008-6215(99)00030-0

  日期：1999.3

  Chlorambucil derivatives involving alkyl 2-aminodeoxy sugars have been synthesized in good yield by coupling the chlorambucil moiety to positions C-2 or C-3 of the sugar, directly or via a spacer. The starting material was easily available from 2-acetamido-2-deoxy-D-glucose. The final compounds were tested for cytotoxicity, and some of those that presented the best results were studied for inhibition of cell proliferation. (C) 1999 Elsevier Science Ltd. All rights reserved.
• ANTAGONISTE SPÉCIFIQUE DE TLR4 DANS LE TRAITEMENT DU MYÉLOME MULTIPLE
  申请人：Etablissement Français du Sang

  公开号：EP3558323A1

  公开（公告）日：2019-10-30
• COMPOSITIONS AND METHODS FOR TREATMENT OF INFLAMMATORY DISORDERS
  申请人：THE JOHNS HOPKINS UNIVERSITY

  公开号：US20180280418A1

  公开（公告）日：2018-10-04

  The present invention relates to methods of treating infectious, inflammatory and post-traumatic disorders by administering various compounds newly discovered to have TLR4 inhibitory activity. In addition to methods of treatment, the present invention further provides for pharmaceutical compositions comprising said compounds, together with a suitable pharmaceutical carrier.