allyl 4,6-O-benzylidene-2-deoxy-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside | 1333477-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: allyl 4,6-O-benzylidene-2-deoxy-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
• CAS: 1333477-10-3
• 化学式: C₃₄H₃₂Cl₃NO₉
• 分子量: 704.988
• InChiKey: CGZMLDLKOWYCAK-NHMJYFFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  47.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  110.78
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  allyl 4,6-O-benzylidene-2-deoxy-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 在 盐酸 、 5-苯基四氮唑 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 allyl 6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a dimeric monosaccharide lipid A mimic and its synergistic effect on the immunostimulatory activity of lipopolysaccharide

  摘要：

  Bacterial endotoxin lipopolysaccharide (LPS) is a potent immune stimulant, with the recognition of LPS and its active principal lipid A mediated by the Toll-like receptor 4 (TLR4)/MD-2 receptor complex. Due to the broad downstream implications of TLR4-mediated signalling, TLR4 ligands show great potential for immunotherapeutic manipulations. In this paper a dimeric monosaccharide lipid A mimic (3) has been designed as a potential TLR4 ligand. The chemical synthesis and the preliminary biological studies are described. Compound 3 shows a significant synergistic effect on LPS-induced ICAM-1 expression in human monocytic THP-1 cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.018
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 4.0h， 以89%的产率得到allyl 4,6-O-benzylidene-2-deoxy-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a dimeric monosaccharide lipid A mimic and its synergistic effect on the immunostimulatory activity of lipopolysaccharide

  摘要：

  Bacterial endotoxin lipopolysaccharide (LPS) is a potent immune stimulant, with the recognition of LPS and its active principal lipid A mediated by the Toll-like receptor 4 (TLR4)/MD-2 receptor complex. Due to the broad downstream implications of TLR4-mediated signalling, TLR4 ligands show great potential for immunotherapeutic manipulations. In this paper a dimeric monosaccharide lipid A mimic (3) has been designed as a potential TLR4 ligand. The chemical synthesis and the preliminary biological studies are described. Compound 3 shows a significant synergistic effect on LPS-induced ICAM-1 expression in human monocytic THP-1 cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.018

文献信息

• Synthesis of the tetrasaccharide repeating unit of the cryoprotectant capsular polysaccharide from <i>Colwellia psychrerythraea</i> 34H
  作者：Giulia Vessella、Angela Casillo、Antonio Fabozzi、Serena Traboni、Alfonso Iadonisi、Maria Michela Corsaro、Emiliano Bedini

  DOI：10.1039/c9ob00104b

  日期：——

  unique capsular polysaccharide (CPS) with anti-freeze properties similar to those of the well-known anti-freeze (glyco)proteins. The tetrasaccharide repeating unit of the CPS – constituted of alternating amino sugars and uronic acid moieties in a glycosaminoglycan-like fashion with an amide-linked threonine (Thr) decoration – was synthesized as an O-n-propyl glycoside. The synthesis faced some challenging

  Colwellia psychrerythraea 34H是一种嗜冷革兰氏阴性细菌，能够通过产生独特的荚膜多糖（CPS）而在零下温度下存活，该荚膜多糖具有与众所周知的抗冻（glyco）蛋白相似的抗冻特性。合成了CPS的四糖重复单元，它是由交替的氨基糖和糖醛酸部分组成，呈类似糖胺聚糖的形式，带有酰胺连接的苏氨酸（Thr）装饰物，被合成为O-正丙基糖苷。合成面临一些挑战性的特征，例如建立拥挤的[→2）α- D -Gal p（1→]部分以及两个尿嘧啶单元仅用于在其中一个区域选择性插入Thr酰胺，得到的四糖的NMR数据证实了拟南芥（C. psychrerythraeaea）多糖的结构。