Acetic acid (2S,3R,4R,5S,6S)-4-acetoxy-5-methoxy-6-methyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester | 136737-89-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3R,4R,5S,6S)-4-acetoxy-5-methoxy-6-methyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester
• CAS: 136737-89-8
• 化学式: C₁₃H₁₈Cl₃NO₇
• 分子量: 406.647
• InChiKey: RHOJOVHEWJJCAB-WXXZGKGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  104.14
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4R,5S,6S)-4-acetoxy-5-methoxy-6-methyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 benzyl 2,4-di-O-acetyl-3-O-[3-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-methyl-α-L-rhamnopyranosyl)-2-O-methyl-α-L-fucopyranosyl]-α-L-rhamnopyranoside
  参考文献：
  名称：

  的Glycopeptidolipid的合成结核分枝一个vium血清型4：一种全合成C-Mycoside GPL的第一例

  摘要：

  glycopeptidolipid（GPL）存在于细胞壁中的制备鸟分枝杆菌血清型4，即3,4-二- ö -Me-α-升-RHA p - （1→1）{ - [R -C 21 ħ 43 CH （OH）CH 2 CO- d -Phe- [4- O -Me-α- l - Rha p-（1→4）-2- O -Me-α- l - Fuc p-（1→3）- α- 1- Rha p-（1→2）-6-脱氧-α- 1 - Tal p-（1→3）]- d -allo-Thr- d -Ala - 1描述了-Alaol}（1）。合成基于将最终结构断开成四个结构单元，即1-鼠李糖基假二肽，6-脱氧-1-戊糖基二肽，三糖供体和3-羟基链烷酸。的关键步骤是三糖供体之间的糖苷键，作为戊烯基糖苷的创建，和6-脱氧升适当的-talose单元d -Phe- ø - （6-脱氧升-talosyl） - d-allo-Thr衍生物和

  DOI：

  10.1021/jo030304e
• 作为产物：
  描述：

  allyl 2,3-di-O-acetyl-4-O-methyl-α-L-rhamnopyranoside 在 Wilkinson's catalyst 三乙烯二胺 、 potassium carbonate 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 Acetic acid (2S,3R,4R,5S,6S)-4-acetoxy-5-methoxy-6-methyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of allyl glycosides for conversion into neoglycoproteins bearing epitopes of mycobacterial glycolipid antigens

  摘要：

  Neoglycoproteins bearing key glycosyl substituents of several glycopeptidolipid antigens of pathogenic Mycobacterium species have been synthesized. Allyl glycosides of the terminal 6-deoxyhexose-containing units of the antigens were prepared, with appropriate ether and ester substituents in place. Ozonolysis of the allyl glycosides was then followed by reductive coupling with epsilon-amino groups of lysine residues in bovine serum albumin, using sodium cyanoborohydride at pH 7.8. The resulting neoglycoproteins emulated the antigenicity of the native molecule in several serological tests.

  DOI：

  10.1016/0008-6215(92)84172-o

文献信息

• Structure–activity relationships of saponin derivatives: A series of entry inhibitors for highly pathogenic H5N1 influenza virus
  作者：Ning Ding、Qing Chen、Wei Zhang、Sumei Ren、Ying Guo、Yingxia Li

  DOI：10.1016/j.ejmech.2012.04.022

  日期：2012.7

  The occurrence of highly pathogenic avian influenza virus H5N1 highlights the urgent need for new classes of antiviral drugs. Theoretically, each of steps in influenza viral life cycle can be a target of antiviral therapeutics. However, up to date, no licenced entry inhibitor drug is available for H5N1 or any other influenza viruses. Our strategy for developing new anti-influenza therapeutics is to target the interaction between HA and sialic acid which is influenza viral receptor presented on host cell surface. Here, based on our previously discovered small molecule inhibitor saponin 1, intensive SAR studies around the sugar chain and aglycone were conducted. The results showed that both the chacotriosyl residue and the chlorogenin moiety of active compound 1 are important for the antiviral activity, although several subtle modifications can be made on particular positions. (C) 2012 Elsevier Masson SAS. All rights reserved.