ethyl 3-O-(2,3,5,6-tetra-O-acetyl-4-thio-β-D-galactofuranosyl)-2-O-benzoyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside | 270917-69-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 3-O-(2,3,5,6-tetra-O-acetyl-4-thio-β-D-galactofuranosyl)-2-O-benzoyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• CAS: 270917-69-6
• 化学式: C₃₆H₄₂O₁₄S₂
• 分子量: 762.853
• InChiKey: ZTQCIFHNJONGNM-SQQQFRCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  52.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  168.42
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-O-(2,3,5,6-tetra-O-acetyl-4-thio-β-D-galactofuranosyl)-2-O-benzoyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 2.5h， 生成 (2S,3R,4R,5R)-2-((R)-1,2-Dihydroxy-ethyl)-5-((2R,4aR,6R,7S,8R,8aR)-6-ethylsulfanyl-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-thiophene-3,4-diol
  参考文献：
  名称：

  Synthesis of oligosaccharide fragments of the glycosylinositolphospholipid of Trypanosoma cruzi: a new selenoglycoside glycosyl donor for the preparation of 4-thiogalactofuranosyl analogues

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(99)00498-x
• 作为产物：
  描述：

  ethyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 、 phenyl 2,3,5,6-tetra-O-acetyl-1-seleno-4-thio-D-galactofuranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以80%的产率得到ethyl 3-O-(2,3,5,6-tetra-O-acetyl-4-thio-β-D-galactofuranosyl)-2-O-benzoyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of oligosaccharide fragments of the glycosylinositolphospholipid of Trypanosoma cruzi: a new selenoglycoside glycosyl donor for the preparation of 4-thiogalactofuranosyl analogues

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(99)00498-x