methyl 3,4-di-O-acetyl-α-D-glucuronatopyranose exo-1,2-O-(ethyl orthoacetate) | 35906-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-acetyl-α-D-glucuronatopyranose exo-1,2-O-(ethyl orthoacetate)
• 英文别名: methyl 3,4-di-O-acetyl-α-D-glucuronatopyranose 1,2-O-(ethyl orthoacetate)；methyl 3,4-di-O-acetyl-α-D-glucuronatopyranose-1,2-(ethyl orthoacetate)；1,2-Ethylorthoacetyl-3,4-di-O-acetyl-α-D-glucopyrenuronsaeure-methylester；1,2-Ethylorthoacetyl-3,4-di-O-acetyl-α-D-glucopyranuronsaeuremethylester；methyl (3aR,5S,6S,7S,7aR)-6,7-diacetyloxy-2-ethoxy-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-carboxylate
• CAS: 35906-40-2
• 化学式: C₁₅H₂₂O₁₀
• 分子量: 362.334
• InChiKey: OTLAOZZFADYSSN-BPZWNZLESA-N

物化性质

• 沸点：
  409.4±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 3,4-di-O-acetyl-α-D-glucuronatopyranose exo-1,2-O-(ethyl orthoacetate) 在 水 、 溶剂黄146 作用下， 反应 0.25h， 以90.6%的产率得到methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate
  参考文献：
  名称：

  Stereoselective Ring-Opening of Acetylated Pyranose-1,2-(etyl orthoacetates).

  摘要：

  当乙酰化的吡喃糖1,2-(乙基邻酸酯)在酸性溶剂中水解时，邻酸酯环的开环受吡喃糖C-4位点的轴向或赤道OAc基团的影响；在酸催化水解过程中，具有C-4轴向OAc基团的3,4,6-三-O-乙酰-α-D-半乳糖吡喃糖-(8)和甲基3,4-二-O-乙酰-α-D-半乳糖酸吡喃糖-1,2-(乙基邻酸酯)(16)分别生成1,3,4,6-四-O-乙酰-α-D-半乳糖吡喃糖(9)和甲基1,3,4-三-O-乙酰-α-D-半乳糖酸吡喃糖(23)，而具有C-4赤道OAc基团的3,4,6-三-O-乙酰-α-D-葡萄糖吡喃糖-(10)和甲基3,4-二-O-乙酰-α-D-葡萄糖醛酸吡喃糖-1,2-(乙基邻酸酯)(22)则分别生成2,3,4,6-四-O-乙酰-D-葡萄糖吡喃糖(11)和甲基2,3,4-三-O-乙酰-D-葡萄糖醛酸吡喃糖(24)。在酸催化水解过程中，具有C-4轴向OAc基团的3,4-二-O-乙酰-β-L-阿拉伯糖吡喃糖-1,2-(乙基邻酸酯)(34)生成1,3,4-三-O-乙酰-β-L-(35)和2,3,4-三-O-乙酰-L-阿拉伯糖吡喃糖(36)的混合物。这些1,2-(邻酸酯)的开环选择性被认为是由1,2-(邻酸)中间体的构象差异以及吡喃糖环上C-4位置的乙酰基团的取向所导致的。

  DOI：

  10.1248/cpb.41.90
• 作为产物：
  描述：

  乙醇 、 乙酰溴-Alpha-D-葡萄糖酮酸甲基酯 在 四丁基溴化铵 作用下， 以 various solvent(s) 为溶剂， 反应 24.0h， 以55%的产率得到methyl 3,4-di-O-acetyl-α-D-glucuronatopyranose exo-1,2-O-(ethyl orthoacetate)
  参考文献：
  名称：

  Preparation of Glycyrrhetic Acid Glycosides Having Various .BETA.(1.RAR.2)-Linked Disaccharides and Their Cytoprotective Effects on Carbon Tetrachloride-Induced Hepatic Injury.

  摘要：

  通过逐步构建法分别合成了 2-O-β-D-吡喃葡萄糖基-β-D-吡喃葡萄糖、2-O-β-D-吡喃半乳糖基-β-D-吡喃葡萄糖、2-O-β-D-吡喃半乳糖基-β-D-吡喃葡萄糖、2-O-β-D-吡喃葡萄糖基-β-D-吡喃葡萄糖、2-O-β-D-吡喃葡萄糖基-β-D-吡喃葡萄糖；从葡萄糖醛酸单糖苷到二糖苷。将苷 1-7 和 2-O-(β-D-吡喃葡萄糖基)-β-D-吡喃葡萄糖基-11-氧代甘草甜素-12-烯-30-酸酯（8）的细胞保护活性与天然存在的甘草甜素（9）进行了比较。在这些苷 1-8 中，苷 3 和苷 7 以 β-D-吡喃葡萄糖（glcUA）为唯一的末端糖成分，是比甘草苷 9 更有效的抗肝损伤材料。

  DOI：

  10.1248/cpb.39.2333

文献信息

• Stereoselective Ring-Opening of Acetylated Pyranose-1,2-(etyl orthoacetates).
  作者：Setsuo SAITO、Shigeya SUMITA、Koki ICHINOSE、Yasuhiko KANDA

  DOI：10.1248/cpb.41.90

  日期：——

  When acetylated pyranose-1, 2-(ethyl orthyl orthoacetates) were hydrolyzed in acidic solvents, the ring-opening of the orthoacetate rings was influenced by the axial or equatorial OAc group at C-4 on the pyranoses; on acid-catalyzed hydrolysis, 3, 4, 6-tri-O-acetyl-α-D-glactopyranose- (8) and methyl 3, 4-di-O-acetyl-α-D-galacturonatopyranose-1, 2-(ethyl orthoacetate) (16) having an axial OAc group at C-4 on the pyranose rings gave 1, 3, 4, 6-tetra-O-acetyl-α-D-galactopyranose (9) and methyl 1, 3, 4-tri-O-acetyl-α-D-galacturonatopyranose (23), respectively, whereas 3, 4, 6-tri-O-acetyl-α-D-glucopyranose- (10) and methyl 3, 4-di-O-acetyl-α-D-glucuronatopyranose-1, 2-(ethyl orthoacetate) (22)having an equatorial OAc group at C-4 on the pyranose rings gave 2, 3, 4, 6-tetra-O-acetyl-D-glucopyranose (11) and methyl 2, 3, 4-tri-O-acetyl-D-glucuronatopyranose (24), respectively. On the acid-catalyzed hydrolysis, 3, 4-di-O-acetyl-β-L-arabinopyranose-1, 2-(ethyl orthoacetate) (34) having an axial OAc group at C-4 on the pyranose ring gave a mixture of 1, 3, 4-tri-O-acetyl-β-L- (35) and 2, 3, 4-tri-O-acetyl-L-arabinopyranose (36). These selectivities of ring-opening of the 1, 2-(orthoacetates) were considered to have resulted from the differences of the conformers fo the 1, 2-(orthoacids)intermediates derived from the 1, 2-(othoacetates) and the orientation of the acetyl groups at C-4 on the pyranose rings.

  当乙酰化的吡喃糖1,2-(乙基邻酸酯)在酸性溶剂中水解时，邻酸酯环的开环受吡喃糖C-4位点的轴向或赤道OAc基团的影响；在酸催化水解过程中，具有C-4轴向OAc基团的3,4,6-三-O-乙酰-α-D-半乳糖吡喃糖-(8)和甲基3,4-二-O-乙酰-α-D-半乳糖酸吡喃糖-1,2-(乙基邻酸酯)(16)分别生成1,3,4,6-四-O-乙酰-α-D-半乳糖吡喃糖(9)和甲基1,3,4-三-O-乙酰-α-D-半乳糖酸吡喃糖(23)，而具有C-4赤道OAc基团的3,4,6-三-O-乙酰-α-D-葡萄糖吡喃糖-(10)和甲基3,4-二-O-乙酰-α-D-葡萄糖醛酸吡喃糖-1,2-(乙基邻酸酯)(22)则分别生成2,3,4,6-四-O-乙酰-D-葡萄糖吡喃糖(11)和甲基2,3,4-三-O-乙酰-D-葡萄糖醛酸吡喃糖(24)。在酸催化水解过程中，具有C-4轴向OAc基团的3,4-二-O-乙酰-β-L-阿拉伯糖吡喃糖-1,2-(乙基邻酸酯)(34)生成1,3,4-三-O-乙酰-β-L-(35)和2,3,4-三-O-乙酰-L-阿拉伯糖吡喃糖(36)的混合物。这些1,2-(邻酸酯)的开环选择性被认为是由1,2-(邻酸)中间体的构象差异以及吡喃糖环上C-4位置的乙酰基团的取向所导致的。
• Preparation of Glycyrrhetic Acid Glycosides Having Various .BETA.(1.RAR.2)-Linked Disaccharides and Their Cytoprotective Effects on Carbon Tetrachloride-Induced Hepatic Injury.
  作者：Setsuo SAITO、Kaoru KURODA、Yasunobu HAYASHI、Yuka SASAKI、Yoichi NAGAMURA、Keiji NISHIDA、Isao ISHIGURO

  DOI：10.1248/cpb.39.2333

  日期：——

  Glycyrrhetic acid glycosides (1-7) having β(1→2)-linked disaccharides such as 2-O-β-D-glucopyranosyl-β-D-galactopyranose, 2-O-β-D-galactopyranosyl-β-D-galactopyranose, 2-O-β-D-glucuronopyranosyl-β-D-galactopyranose, 2-O-β-D-glucopyranosyl-β-D-glucuronopyranose, 2-O-β-D-galactopyranosyl-β-D-glucuronopyranose, 2-O-β-D-galactopyranosyl-β-D-glucopyranose, 2-O-β-D-glucuronopyranosyl-β-D-glucopyranose, respectively, were synthesized by stepwise construction; from glucyrrhetic acid monoglycosides to the diglycosides. The cytoprotective activities of the glycosides 1-7 and 2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl-11-oxoolean-12-en-30-oate (8) were compared with natural occurring glycyrrhizin (9). Among these glycosides 1-8, glycosides 3 and 7 having β-D-glucuronopyranose (glcUA) as the only terminal sugar component were more effective materials against hepatic injury than glycyrrhizin 9.

  通过逐步构建法分别合成了 2-O-β-D-吡喃葡萄糖基-β-D-吡喃葡萄糖、2-O-β-D-吡喃半乳糖基-β-D-吡喃葡萄糖、2-O-β-D-吡喃半乳糖基-β-D-吡喃葡萄糖、2-O-β-D-吡喃葡萄糖基-β-D-吡喃葡萄糖、2-O-β-D-吡喃葡萄糖基-β-D-吡喃葡萄糖；从葡萄糖醛酸单糖苷到二糖苷。将苷 1-7 和 2-O-(β-D-吡喃葡萄糖基)-β-D-吡喃葡萄糖基-11-氧代甘草甜素-12-烯-30-酸酯（8）的细胞保护活性与天然存在的甘草甜素（9）进行了比较。在这些苷 1-8 中，苷 3 和苷 7 以 β-D-吡喃葡萄糖（glcUA）为唯一的末端糖成分，是比甘草苷 9 更有效的抗肝损伤材料。