ethyl 2-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside | 852311-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside
• CAS: 852311-78-5
• 化学式: C₁₇H₃₄O₄SSi
• 分子量: 362.606
• InChiKey: IIUMXTBBTRMIPM-VYDRJRHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 在 4 A molecular sieve 、 四丁基氟化铵 、 四丁基溴化铵 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 166.0h， 生成 6-[N-(benzyloxycarbonylamino)hexyl]-2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-[3,4-O-isopropylidene-2-O-(3,4-O-isopropylidene-α-L-fucopyranosyl)-α-L-fucopyranosyl]-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and antibody-binding studies of a series of parasite fuco-oligosaccharides

  摘要：

  Complex multifucosylated oligosaccharides are structural elements of glycoprotein and glycolipid subsets of larval, egg, and adult stages of Schistosoma, the parasitic worms that cause schistosomiasis, a serious disease affecting more than 200 million people in the tropics. The fucosylated structures are thought to play an important role in the immunology of schistosomiasis. Defined schistosomal oligosaccharides that enable immunological studies are difficult to obtain from natural sources. Therefore, we have chemically synthesized spacer-linked GlcNAc, Fuc alpha 1-2Fuc alpha 1-3GlcNAc, Fuc alpha 1-2Fuc alpha 1-3GlcNAc, and Fuc alpha 1-2Fuc alpha 1-2Fuc alpha 1-3GlcNAc. This series of linear oligosaccharides was used to screen a library of anti-schistosome monoclonal antibodies by surface plasmon resonance spectroscopy. Interestingly, the reactive antibodies could be grouped according to their specificity for the different oligosaccharides tested, showing that these oligosaccharides form different immunological entities based on the number and linkage of the fucose residues. Subsequently, the thus defined monoclonal antibodies were used to visualize the expression of the corresponding oligosaccharide epitopes by adult Schistosoma mansoni worms. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.009
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 ethyl 3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以89%的产率得到ethyl 2-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Synthesis and antibody-binding studies of a series of parasite fuco-oligosaccharides

  摘要：

  Complex multifucosylated oligosaccharides are structural elements of glycoprotein and glycolipid subsets of larval, egg, and adult stages of Schistosoma, the parasitic worms that cause schistosomiasis, a serious disease affecting more than 200 million people in the tropics. The fucosylated structures are thought to play an important role in the immunology of schistosomiasis. Defined schistosomal oligosaccharides that enable immunological studies are difficult to obtain from natural sources. Therefore, we have chemically synthesized spacer-linked GlcNAc, Fuc alpha 1-2Fuc alpha 1-3GlcNAc, Fuc alpha 1-2Fuc alpha 1-3GlcNAc, and Fuc alpha 1-2Fuc alpha 1-2Fuc alpha 1-3GlcNAc. This series of linear oligosaccharides was used to screen a library of anti-schistosome monoclonal antibodies by surface plasmon resonance spectroscopy. Interestingly, the reactive antibodies could be grouped according to their specificity for the different oligosaccharides tested, showing that these oligosaccharides form different immunological entities based on the number and linkage of the fucose residues. Subsequently, the thus defined monoclonal antibodies were used to visualize the expression of the corresponding oligosaccharide epitopes by adult Schistosoma mansoni worms. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.009