2-[3-((2R,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-isoindole-1,3-dione | 654644-91-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[3-((2R,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-isoindole-1,3-dione
• CAS: 654644-91-4
• 化学式: C₄₅H₄₅NO₇
• 分子量: 711.855
• InChiKey: DZINLCFBSBLDAN-UMCCLHMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  53.0
• 可旋转键数：
  17.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.53
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-[3-((2R,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-isoindole-1,3-dione 在 4-二甲氨基吡啶 、 一水合肼 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 2-[2-((5Z,9Z,14Z)-3,3,7,8,12,13,17,18-Octaethyl-22,24-dihydro-3H-benzo[at]porphin-21-yl)-ethoxy]-N-[3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-acetamide
  参考文献：
  名称：

  Functionalization of OEP-Based Benzochlorins To Develop Carbohydrate-Conjugated Photosensitizers. Attempt To Target β-Galactoside-Recognized Proteins

  摘要：

  meso-(2-Formylvinyl)octaethylporphyrin on reaction with cyanotrimethylsilane in the presence of various catalysts {copper triflate [Cu(OTf)(2)], indium triflate [In(OTf)(3)], or magnesium bromide diethyl etherate (MgBr2.Et2O)} produced a mixture of the intermediate 3-hydroxy-3-cyanopropenoporphyrin, the corresponding trimethylsilyl ether derivative, and the unexpected propenochlorins. The yields of the reaction products were found to depend on the reaction conditions and the catalysts used. The intermediate porphyrins on treatment with concentrated sulfuric acid yielded the freebase cyanobenzochlorins in major quantity along with several other novel benzochlorins as minor products. Reduction of ethyl-3-hydroxy-1-pentenoate-porphyrin with DIBAL-H/NaBH4 and subsequent acid treatment provided the corresponding free-base 10(3)-(2-hydroxyethyl)benzochlorin, which upon a sequence of reactions gave a free-base benzochlorin bearing a carboxylic acid functionality in good yield. It was then condensed with a variety of carbohydrates (glucosamine, galactosamine, and lactosamine), and the related conjugates were screened using the galectin-binding-ability assay. Among the carbohydrate conjugates investigated, the lactose and galactose analogues displayed the galectin-binding ability with an enhancement of about 300-400-fold compared to lactose. In preliminary studies, all photosensitizers (with or without carbohydrate moieties) were found to be active in vitro [radiation-induced fibrosarcoma (RIF) tumor cells]. However, the cells incubated with lactose (known to bind to beta-galactoside-recognized proteins) prior to the addition of the photosensitizers containing the beta-galactose moiety (e.g., galactose and lactose) produced a 100% decrease in their photosensitizing efficacy. Under similar experimental conditions, benzochlorin without a beta-galactoside moiety or the related glucose conjugate did not show any inhibition in its photosensitizing efficacy. These results in combination with the galectin-binding data indicate a possible beta-galactoside-recognized protein specificity of the galactose- and lactosebenzochlorin conjugates.

  DOI：

  10.1021/jo030280b
• 作为产物：
  描述：

  邻苯二甲酸亚胺 、 3-(tetra-O-benzyl-α-D-galactopyranosyl)-1-propanol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以79%的产率得到2-[3-((2R,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-isoindole-1,3-dione
  参考文献：
  名称：

  Functionalization of OEP-Based Benzochlorins To Develop Carbohydrate-Conjugated Photosensitizers. Attempt To Target β-Galactoside-Recognized Proteins

  摘要：

  meso-(2-Formylvinyl)octaethylporphyrin on reaction with cyanotrimethylsilane in the presence of various catalysts {copper triflate [Cu(OTf)(2)], indium triflate [In(OTf)(3)], or magnesium bromide diethyl etherate (MgBr2.Et2O)} produced a mixture of the intermediate 3-hydroxy-3-cyanopropenoporphyrin, the corresponding trimethylsilyl ether derivative, and the unexpected propenochlorins. The yields of the reaction products were found to depend on the reaction conditions and the catalysts used. The intermediate porphyrins on treatment with concentrated sulfuric acid yielded the freebase cyanobenzochlorins in major quantity along with several other novel benzochlorins as minor products. Reduction of ethyl-3-hydroxy-1-pentenoate-porphyrin with DIBAL-H/NaBH4 and subsequent acid treatment provided the corresponding free-base 10(3)-(2-hydroxyethyl)benzochlorin, which upon a sequence of reactions gave a free-base benzochlorin bearing a carboxylic acid functionality in good yield. It was then condensed with a variety of carbohydrates (glucosamine, galactosamine, and lactosamine), and the related conjugates were screened using the galectin-binding-ability assay. Among the carbohydrate conjugates investigated, the lactose and galactose analogues displayed the galectin-binding ability with an enhancement of about 300-400-fold compared to lactose. In preliminary studies, all photosensitizers (with or without carbohydrate moieties) were found to be active in vitro [radiation-induced fibrosarcoma (RIF) tumor cells]. However, the cells incubated with lactose (known to bind to beta-galactoside-recognized proteins) prior to the addition of the photosensitizers containing the beta-galactose moiety (e.g., galactose and lactose) produced a 100% decrease in their photosensitizing efficacy. Under similar experimental conditions, benzochlorin without a beta-galactoside moiety or the related glucose conjugate did not show any inhibition in its photosensitizing efficacy. These results in combination with the galectin-binding data indicate a possible beta-galactoside-recognized protein specificity of the galactose- and lactosebenzochlorin conjugates.

  DOI：

  10.1021/jo030280b