2-propyl 6-O-acetyl-3-deoxy-4-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-4-thio-α-D-threo-hexopyranosid-2-ulose | 1153941-03-7

• 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: 2-propyl 6-O-acetyl-3-deoxy-4-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-4-thio-α-D-threo-hexopyranosid-2-ulose
• CAS: 1153941-03-7
• 化学式: C₄₅H₄₄O₁₄S
• 分子量: 840.902
• InChiKey: PTEPAEJMLKBMAY-MXYWXHAASA-N

物化性质

• 沸点：
  899.8±65.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  60.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  176.26
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  2-propyl 6-O-acetyl-3-deoxy-4-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-4-thio-α-D-threo-hexopyranosid-2-ulose 在 sodium tetrahydroborate 、 Dowex 50 (H+) resin 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以41%的产率得到2-propyl 6-O-acetyl-3-deoxy-4-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-4-thio-α-D-xylohexopyranoside
  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：

  (R)-1-((2S,3S,4R,5S)-3,4-bis(benzoyloxy)-5-(carbamimidoylthio)tetrahydrofuran-2-yl)ethane-1,2-diyl dibenzoate 、 (2S,6S)-6-acetoxymethyl-2-(2-propyloxy)-2H-pyran-3(6H)-one 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以52%的产率得到2-propyl 6-O-acetyl-3-deoxy-4-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-4-thio-α-D-threo-hexopyranosid-2-ulose
  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