methyl 2,3,4-tri-O-benzoyl-6-S-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)-6-thio-α-D-galactoyranoside | 1153940-88-5

• 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-benzoyl-6-S-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)-6-thio-α-D-galactoyranoside
• CAS: 1153940-88-5
• 化学式: C₃₉H₄₀O₁₅S
• 分子量: 780.804
• InChiKey: LOHAWNWOJTZZTI-GIZYYZCTSA-N

物化性质

• 沸点：
  831.4±65.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  55.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  185.49
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-6-S-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)-6-thio-α-D-galactoyranoside 在 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 以77%的产率得到methyl 6-S-(α-L-arabinofuranosyl)-6-thio-α-D-galactopyranoside
  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：

  1,2,3,5-四-O-乙酰基-Alpha-L-阿拉伯呋喃糖 、 methyl 2,3,4-tri-O-benzoyl-6-thio-α-D-galactopyranoside 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 4.17h， 以61%的产率得到methyl 2,3,4-tri-O-benzoyl-6-S-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)-6-thio-α-D-galactoyranoside
  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