Galf2Ac3Ac5Ac6Ac(b1-6)[Bn(-2)][Bn(-3)][Bn(-4)]Man(a)-SPh | 946839-59-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Galf2Ac3Ac5Ac6Ac(b1-6)[Bn(-2)][Bn(-3)][Bn(-4)]Man(a)-SPh
• 英文别名: [(2R)-2-acetyloxy-2-[(2S,3S,4R,5R)-3,4-diacetyloxy-5-[[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-phenylsulfanyloxan-2-yl]methoxy]oxolan-2-yl]ethyl] acetate
• CAS: 946839-59-4
• 化学式: C₄₇H₅₂O₁₄S
• 分子量: 872.987
• InChiKey: ARQMBRLLEGBEET-WVAMMWBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  62
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  186
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Galf2Ac3Ac5Ac6Ac(b1-6)[Bn(-2)][Bn(-3)][Bn(-4)]Man(a)-SPh 在 sodium methylate 作用下， 以 水 为溶剂， 以65 mg的产率得到phenyl β-D-galactofuranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of galactofuranose-containing disaccharides using thioimidoyl-type donors

  摘要：

  Four galactofuranose-containing disaccharides have been prepared utilising various thioimidates [Galf-SC(=NR)XR'] and suitably protected acceptors as key precursors. We observed that the efficiency of the coupling reactions was particularly dependent on the aglycon present on the furanosyl donor when copper(II) ions were used as the promoter, and that activation could be correlated with the nature of the third heteroatorn, X. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.10.001
• 作为产物：
  描述：

  1,2,3,5,6-penta-O-acetyl-D-galactofuranose 在 三氟化硼乙醚 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 生成 Galf2Ac3Ac5Ac6Ac(b1-6)[Bn(-2)][Bn(-3)][Bn(-4)]Man(a)-SPh
  参考文献：
  名称：

  Synthesis of galactofuranose-containing disaccharides using thioimidoyl-type donors

  摘要：

  Four galactofuranose-containing disaccharides have been prepared utilising various thioimidates [Galf-SC(=NR)XR'] and suitably protected acceptors as key precursors. We observed that the efficiency of the coupling reactions was particularly dependent on the aglycon present on the furanosyl donor when copper(II) ions were used as the promoter, and that activation could be correlated with the nature of the third heteroatorn, X. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.10.001

文献信息

• First <i>O</i>-Glycosylation from Unprotected 1-Thioimidoyl Hexofuranosides Assisted by Divalent Cations
  作者：Ronan Euzen、Jean-Paul Guégan、Vincent Ferrières、Daniel Plusquellec

  DOI：10.1021/jo070741j

  日期：2007.7.1

  The preparation of O-hexofuranosides was accomplished from unprotected 1-thioimidoyl furanosides as donors. The present methodology was first used for the synthesis of octyl galactofuranoside and further extended to D-galactofuranose-containing disaccharides. Within this study, we emphasized the need for additional complexing cations to maintain the furanose ring in its initial size. After experimentation, calcium ion was first used concomitantly with trimethylsilyl trifluoromethanesulfonate, the latter being able to activate the thioimidate and the former being likely to inhibit ring expansion. Moreover, an improvement was performed by using copper(II) trifluoromethanesulfonate which could then meet the requirements as both promoter and complexing agent.