1,2:3,4-di-O-isopropylidene-6-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-6-thio-α-D-galactopyranose | 1153940-53-4

• 分子结构分类: 有机化合物
• 英文名称: 1,2:3,4-di-O-isopropylidene-6-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-6-thio-α-D-galactopyranose
• CAS: 1153940-53-4
• 化学式: C₄₆H₄₆O₁₄S
• 分子量: 854.929
• InChiKey: DWEHDWXNJAGOGY-MLKSZVIPSA-N

物化性质

• 沸点：
  883.7±65.0 °C(predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  61.0
• 可旋转键数：
  13.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  160.58
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  1,2:3,4-di-O-isopropylidene-6-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-6-thio-α-D-galactopyranose 在 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 以91%的产率得到1,2:3,4-di-O-isopropylidene-6-S-(β-D-galactofuranosyl)-6-thio-α-D-galactopyranose
  参考文献：
  名称：

  Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase

  摘要：

  Thiodisaccharides having beta-D-Galf or alpha-L-Araf units as non-reducing end have been synthesized by the SnCl4- or MoO2Cl2-promoted thioglycosylation of per-O-benzoyl-D-galactofuranose (1), its 1-O-acetyl analogue 4, or per-O-acetyl-alpha-L-arabinofuranose (16) with 6-thioglucose or 6-thiogalactose derivatives. After convenient removal of the protecting groups, the free thiodisaccharides having the basic structure beta-D-Galf(1 -> 6)-6-thio-alpha-D-Glcp-OMe (5) or beta-D-Galf(1 -> 6)-6-thio-alpha-D-Galp-OMe (15) were obtained. The respective alpha-L-Araf analogues 18 and 20 were prepared similarly from 16. Alternatively, beta-D-Galf(1 -> 4)-4-thio- 3-deoxy-alpha-L-Xylp-OiPr was synthesized by Michael addition to a sugar enone of 1-thio-beta-D-Galf derivative, generated in situ from the glycosyl isothiourea derivative of 1. The free S-linked disaccharides were evaluated as inhibitors of the beta-galactofuranosidase from Penicillium fellutanum, being 15 and 20 the more active inhibitors against this enzyme. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.045
• 作为产物：
  描述：

  1,2:3,4-二-o-异亚丙基-6-硫代-a-d-吡喃葡萄糖 、 1-O-Acetyl-2,3,4,6-tetra-O-benzoyl-β-galactofuranose 在 二氯二氧化钼 作用下， 以 二氯甲烷 为溶剂， 反应 24.17h， 以37%的产率得到1,2:3,4-di-O-isopropylidene-6-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-6-thio-α-D-galactopyranose
  参考文献：
  名称：

  Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase

  摘要：

  Thiodisaccharides having beta-D-Galf or alpha-L-Araf units as non-reducing end have been synthesized by the SnCl4- or MoO2Cl2-promoted thioglycosylation of per-O-benzoyl-D-galactofuranose (1), its 1-O-acetyl analogue 4, or per-O-acetyl-alpha-L-arabinofuranose (16) with 6-thioglucose or 6-thiogalactose derivatives. After convenient removal of the protecting groups, the free thiodisaccharides having the basic structure beta-D-Galf(1 -> 6)-6-thio-alpha-D-Glcp-OMe (5) or beta-D-Galf(1 -> 6)-6-thio-alpha-D-Galp-OMe (15) were obtained. The respective alpha-L-Araf analogues 18 and 20 were prepared similarly from 16. Alternatively, beta-D-Galf(1 -> 4)-4-thio- 3-deoxy-alpha-L-Xylp-OiPr was synthesized by Michael addition to a sugar enone of 1-thio-beta-D-Galf derivative, generated in situ from the glycosyl isothiourea derivative of 1. The free S-linked disaccharides were evaluated as inhibitors of the beta-galactofuranosidase from Penicillium fellutanum, being 15 and 20 the more active inhibitors against this enzyme. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.045