methyl 2,3,4-tri-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside | 157865-35-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside
• 英文别名: methyl 2,3,4-tri-O-(p-methoxybenzyl)-1-thio-β-L-fucopyranoside；(2S,3R,4R,5S,6R)-3,4,5-tris[(4-methoxyphenyl)methoxy]-2-methyl-6-methylsulfanyloxane
• CAS: 157865-35-5
• 化学式: C₃₁H₃₈O₇S
• 分子量: 554.705
• InChiKey: NVTXCJWIBXADPE-KCQURFMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲烷磺酸甲酯 作用下， 以 various solvent(s) 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis of complex-type glycans derived from parasitic helminths

  摘要：

  Chemical synthesis of complex-type glycans 1 and 2 derived from eggs of parasitic helminths, Schistosoma mansoni and Schistosoma japonicum, is described. These branched sugar chains were synthesized regio- and stereo selectively by using beta-mannosylation, desilylation under high pressure, and glycosylation in frozen solvent as key transformations. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.100
• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-1-硫代-β-L-岩藻糖苷甲酯 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 methyl 2,3,4-tri-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of 5-Thio-l-fucose-Containing Disaccharides, as Sequence-Specific Inhibitors, and 2‘-Fucosyllactose, as a Substrate of α-l-Fucosidases

  摘要：

  Four 5-thio-L-fucose-containing disaccharides having alpha(1-->6), alpha(1-->3), alpha(1-->4)GlcNAc, and alpha(1-->2-Gal linkages (compounds 1-4, respectively) were synthesized as potential alpha-L-fucosidase inhibitors. The glycosylation reactions using 2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate as a glycosyl donor and BF3 . OEt(2) as a catalyst gave mainly alpha-linked disaccharides. Only alpha(1-->2)-linked disaccharide 4 showed inhibitory activity (K-i = 0.21 mM) against Bacillus alpha-L-fucosidase which hydrolyzes the Fuc alpha(1-->2) linkage specifically. The results suggested that sequence specificity of an enzyme could be estimated from the inhibitory activities of the compounds 1-4. In contrast, every disaccharide showed inhibitory activity (K-i = 30-91 mu M) against bovine epididymis alpha-L-fucosidase.

  DOI：

  10.1021/jo961725h

文献信息

• Synthesis of methyl O-(β-d-galactopyranosyl)-(1→3)-O-[α-l-fucopyranosyl-(1→4)]-2-acetamido-2-deoxy-6-O-sulfoβ -d-glucopyranoside sodium salt as a potential ligand for selectin molecules
  作者：Rakesh Vig、Rakesh K. Jain、Khushi L. Matta

  DOI：10.1016/0008-6215(94)00258-h

  日期：1995.1
• Synthesis of 5-Thio-<scp>l</scp>-fucose-Containing Disaccharides, as Sequence-Specific Inhibitors, and 2‘-Fucosyllactose, as a Substrate of α-<scp>l</scp>-Fucosidases
  作者：Masayuki Izumi、Osamu Tsuruta、Satoru Harayama、Hironobu Hashimoto

  DOI：10.1021/jo961725h

  日期：1997.2.1

  Four 5-thio-L-fucose-containing disaccharides having alpha(1-->6), alpha(1-->3), alpha(1-->4)GlcNAc, and alpha(1-->2-Gal linkages (compounds 1-4, respectively) were synthesized as potential alpha-L-fucosidase inhibitors. The glycosylation reactions using 2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate as a glycosyl donor and BF3 . OEt(2) as a catalyst gave mainly alpha-linked disaccharides. Only alpha(1-->2)-linked disaccharide 4 showed inhibitory activity (K-i = 0.21 mM) against Bacillus alpha-L-fucosidase which hydrolyzes the Fuc alpha(1-->2) linkage specifically. The results suggested that sequence specificity of an enzyme could be estimated from the inhibitory activities of the compounds 1-4. In contrast, every disaccharide showed inhibitory activity (K-i = 30-91 mu M) against bovine epididymis alpha-L-fucosidase.
• Synthesis of complex-type glycans derived from parasitic helminths
  作者：Jun Nakano、Hiromichi Ohta、Yukishige Ito

  DOI：10.1016/j.bmcl.2005.10.100

  日期：2006.2

  Chemical synthesis of complex-type glycans 1 and 2 derived from eggs of parasitic helminths, Schistosoma mansoni and Schistosoma japonicum, is described. These branched sugar chains were synthesized regio- and stereo selectively by using beta-mannosylation, desilylation under high pressure, and glycosylation in frozen solvent as key transformations. (c) 2005 Elsevier Ltd. All rights reserved.