5-acetamido-2,4,9-tri-O-pivaloyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosono-1,7-lactone | 121409-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5-acetamido-2,4,9-tri-O-pivaloyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosono-1,7-lactone
• 英文别名: [(2R)-2-[(1R,2R,5R,7S,8R)-8-acetamido-5,7-bis(2,2-dimethylpropanoyloxy)-4-oxo-3,9-dioxabicyclo[3.3.1]nonan-2-yl]-2-hydroxyethyl] 2,2-dimethylpropanoate
• CAS: 121409-27-6
• 化学式: C₂₆H₄₁NO₁₁
• 分子量: 543.612
• InChiKey: AOLOZCLXPDMXLC-KNELIFBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  163.76
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  N-acetyl neuraminic acid 、 三甲基乙酰氯 生成 5-acetamido-2,4,9-tri-O-pivaloyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosono-1,7-lactone
  参考文献：
  名称：

  SATO, SHINGO;FURUHATA, KIMIO;OGURA, HARUO, CHEM. AND PHARM. BULL., 36,(1988) N2, C. 4678-4688

  摘要：

  DOI：

文献信息

• Studies on sialic acids. XIV. Lactone derivatives of N-acetylneuraminic acid.
  作者：SHINGO SATO、KIMIO FURUHATA、HARUO OGURA

  DOI：10.1248/cpb.36.4678

  日期：——

  Benzoylation of N-acetylneuraminic acid (Neu5Ac) gave a variety of partially benzoylated bicyclic 1, 7-lactone derivatives and a perbenzoylated bicyclic 1, 4-lactone derivative in good yields. The structures of these compounds were elucidated mainly by means of proton nuclear magnetic resonance spectroscopy.Further, pivaloylation and ethoxycarbonylation of Neu5Ac also gave the corresponding acylated bicyclic lactone derivatives.These results allowed us to postulate a mechanism for the formation of bicyclic lactone derivatives in the acylation of Neu5Ac. Furthermore, treatment of Neu5Ac with diazomethane in an acidic methanol solution gave methyl a-D-neuraminoside methyl ester and a monocyclic 2-O-methyl-y-lactone derivative in 18% and 29% yields, respectively.These results provided information about the equilibrium of Neu5Ac in basic and acidic media.

  N-acetyl neuraminic acid（Neu5Ac）苯甲酰化反应产生了多种部分苯甲酰化的双环 1，7-内酯衍生物和一种全苯甲酰化的双环 1，4-内酯衍生物，产率良好。此外，Neu5Ac 的新戊酰化和乙氧基羰基化也得到了相应的酰化双环内酯衍生物。这些结果使我们能够推测 Neu5Ac酰化过程中双环内酯衍生物的形成机制。此外，在酸性甲醇溶液中用重氮甲烷处理 Neu5Ac，可得到甲基 a-D-神经氨酸甲酯和单环 2-O-甲基内酯衍生物，收率分别为 18% 和 29%。