ethyl 2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-4,6-O-benzylidene-1-thio-α-D-mannopyranoside | 270917-79-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• 英文别名: (2R,4aR,6R,7S,8S,8aS)-6-[[(2R,4aR,6R,7S,8S,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]oxy]-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 270917-79-8
• 化学式: C₃₅H₄₀O₁₀S
• 分子量: 652.763
• InChiKey: VPKARLOOMVESGI-GLJBDULJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  46
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 palladium on activated charcoal N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 氨 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.67h， 生成 ethyl β-D-galactofuranosyl-(1->3)-α-D-mannopyranosyl-(1->2)-[β-D-galactofuranosyl-(1->3)]-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of galactofuranosyl-containing oligosaccharides corresponding to the glycosylinositolphospholipid of Trypanosomacruzi

  摘要：

  The oligosaccharide beta-D-Ga1f-(1-->3)-alpha-D-Manp-(1-->2)-[beta-D-Ga1f-(1-->3)]-alpha-D-Manp-(1-->2)-alpha-D-Manp corresponds to the terminal end of the glycosylinositolphospholipid oligosaccharide of the protozoan Trypanosoma cruzi, the causative agent of Chagas' disease. Syntheses of methyl or ethylthio glycosides of the terminal disaccharide, trisaccharide, tetrasaccharide, and pentasaccharide corresponding to this structure are described. These syntheses employ the selective activation of a phenyl 1-selenogalactofuranoside or a phenyl 1-selenomannopyranoside donor over ethyl 1-thioglycoside accepters with NIS-TfOH. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00007-0
• 作为产物：
  描述：

  phenyl 4,6-O-benzylidene-1-seleno-α-D-mannopyranoside 在 4-二甲氨基吡啶 、 sodium hydroxide 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium methylate 、 四丁基硫酸氢铵 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 41.5h， 生成 ethyl 2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of galactofuranosyl-containing oligosaccharides corresponding to the glycosylinositolphospholipid of Trypanosomacruzi

  摘要：

  The oligosaccharide beta-D-Ga1f-(1-->3)-alpha-D-Manp-(1-->2)-[beta-D-Ga1f-(1-->3)]-alpha-D-Manp-(1-->2)-alpha-D-Manp corresponds to the terminal end of the glycosylinositolphospholipid oligosaccharide of the protozoan Trypanosoma cruzi, the causative agent of Chagas' disease. Syntheses of methyl or ethylthio glycosides of the terminal disaccharide, trisaccharide, tetrasaccharide, and pentasaccharide corresponding to this structure are described. These syntheses employ the selective activation of a phenyl 1-selenogalactofuranoside or a phenyl 1-selenomannopyranoside donor over ethyl 1-thioglycoside accepters with NIS-TfOH. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00007-0

文献信息

• Synthesis of oligosaccharide fragments of the glycosylinositolphospholipid of Trypanosoma cruzi: a new selenoglycoside glycosyl donor for the preparation of 4-thiogalactofuranosyl analogues
  作者：Karla D Randell、Blair D Johnston、Ernest E Lee、B.Mario Pinto

  DOI：10.1016/s0957-4166(99)00498-x

  日期：2000.1

  A new selenoglycoside, phenyl 2,3,5,6-tetra-O-acetyl-4-thio-1-selenogalactofuranose, has been synthesized. This 4-thiogalactofuranosyl donor was used in the syntheses of heteroatom analogues of the di-, tri-, and tetrasaccharides corresponding to the oligosaccharide beta-D-Galf-(1-->3)-alpha-D-Manp-(1-->2)-(beta-D-Galf-(1-->3))-alpha-D-Manp. These compounds represent fragments of the terminal end of the glycosylinositolphospholipid oligosaccharide found in the protozoan Trypanosoma cruzi, the causative agent of Chagas disease, and are intended for use as inhibitors of the enzymes that construct the native oligosaccharides. The syntheses employed the selective activation of a phenyl 4-thio-1-selenogalactofuranoside glycosyl donor over ethyl 1-thioglycoside glycosyl accepters with NIS/TfOH. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of galactofuranosyl-containing oligosaccharides corresponding to the glycosylinositolphospholipid of Trypanosomacruzi
  作者：Karla D. Randell、Blair D. Johnston、Paula N. Brown、B.Mario Pinto

  DOI：10.1016/s0008-6215(00)00007-0

  日期：2000.5

  The oligosaccharide beta-D-Ga1f-(1-->3)-alpha-D-Manp-(1-->2)-[beta-D-Ga1f-(1-->3)]-alpha-D-Manp-(1-->2)-alpha-D-Manp corresponds to the terminal end of the glycosylinositolphospholipid oligosaccharide of the protozoan Trypanosoma cruzi, the causative agent of Chagas' disease. Syntheses of methyl or ethylthio glycosides of the terminal disaccharide, trisaccharide, tetrasaccharide, and pentasaccharide corresponding to this structure are described. These syntheses employ the selective activation of a phenyl 1-selenogalactofuranoside or a phenyl 1-selenomannopyranoside donor over ethyl 1-thioglycoside accepters with NIS-TfOH. (C) 2000 Elsevier Science Ltd. All rights reserved.