(2S,3R,4S,5S,6S)-2-(([1,1'-biphenyl]-3-carbonyl)oxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1105557-03-6

• 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: (2S,3R,4S,5S,6S)-2-(([1,1'-biphenyl]-3-carbonyl)oxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1105557-03-6
• 化学式: C₂₆H₂₆O₁₁
• 分子量: 514.486
• InChiKey: DXHRRMQSFYWHHU-ULKMUXEJSA-N

物化性质

• 沸点：
  598.6±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S,6S)-2-(([1,1'-biphenyl]-3-carbonyl)oxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 Aspergillus niger lipase AS Amano 作用下， 以 二甲基亚砜 为溶剂， 反应 0.28h， 以83%的产率得到methyl 1-O-(m-phenyl)benzoyl-2,4-di-O-acetyl-β-D-glucopyranuronate
  参考文献：
  名称：

  Characterization of chemo- and regioselectivity in enzyme-catalyzed consecutive hydrolytic deprotection of methyl acetyl derivatives of 1-β-O-acyl glucuronides

  摘要：

  Methyl acetyl derivatives of 1-beta-O-(o-, m-, or p-phenyl)benzoyl glucuronides 2a-c are fully deprotected by a one-pot consecutive enzyme-catalyzed hydrolytic reaction to afford 4a-c, without isolation of the O-deacetylated derivatives 3a-c. A lipase AS Amano from Aspergillus niger (LAS) and a carboxylesterase from Streptomyces rochei (CSR) showed high chemoselectivity toward the O-deacetylation of the o- and m-isomers, respectively. Chemoselective O-deacetylation of the p-isomer was promoted only in the presence of both enzymes. A lipase type B from Candida antarctica (CALB) was effective for the subsequent enzymatic hydrolysis of the methyl esters of 3a-c. LAS exhibited also regioselective 3-O-deacetylation activity to afford the corresponding 2,4-di-O-acetyl intermediates 5a-c, for which CSR showed higher O-deacetylation activity than that for 2a-c. In kinetic studies using p-nitrophenyl ester substrates, LAS exhibited a broader acyl preference, the octanoyl ester being most effectively hydrolysed, whereas CSR exhibited the highest hydrolytic activity toward the acetyl ester. LAS and CSR play complementary as well as synergistic roles in the O-deacetylation of 2 bearing R groups of different steric bulkiness. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.12.014
• 作为产物：
  描述：

  (2S,3R,4S,5S,6S)-2-(([1,1'-biphenyl]-2-carbonyl)oxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 Aspergillus niger lipase AS Amano 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 (2S,3R,4S,5S,6S)-2-(([1,1'-biphenyl]-3-carbonyl)oxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Characterization of chemo- and regioselectivity in enzyme-catalyzed consecutive hydrolytic deprotection of methyl acetyl derivatives of 1-β-O-acyl glucuronides

  摘要：

  Methyl acetyl derivatives of 1-beta-O-(o-, m-, or p-phenyl)benzoyl glucuronides 2a-c are fully deprotected by a one-pot consecutive enzyme-catalyzed hydrolytic reaction to afford 4a-c, without isolation of the O-deacetylated derivatives 3a-c. A lipase AS Amano from Aspergillus niger (LAS) and a carboxylesterase from Streptomyces rochei (CSR) showed high chemoselectivity toward the O-deacetylation of the o- and m-isomers, respectively. Chemoselective O-deacetylation of the p-isomer was promoted only in the presence of both enzymes. A lipase type B from Candida antarctica (CALB) was effective for the subsequent enzymatic hydrolysis of the methyl esters of 3a-c. LAS exhibited also regioselective 3-O-deacetylation activity to afford the corresponding 2,4-di-O-acetyl intermediates 5a-c, for which CSR showed higher O-deacetylation activity than that for 2a-c. In kinetic studies using p-nitrophenyl ester substrates, LAS exhibited a broader acyl preference, the octanoyl ester being most effectively hydrolysed, whereas CSR exhibited the highest hydrolytic activity toward the acetyl ester. LAS and CSR play complementary as well as synergistic roles in the O-deacetylation of 2 bearing R groups of different steric bulkiness. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.12.014