5-acetamido-2,4,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosono-1,7-lactone | 116058-22-1

• 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: 5-acetamido-2,4,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosono-1,7-lactone
• 英文别名: 5-acetamido-2,4,8,9-tetra-O-acetyl-β-D-glycero-D-galacto-2-nonulopyranosonic acid-1,7-lactone；[(2R)-2-[(1R,2S,5R,7S,8R)-8-acetamido-5,7-diacetyloxy-4-oxo-3,9-dioxabicyclo[3.3.1]nonan-2-yl]-2-acetyloxyethyl] acetate
• CAS: 116058-22-1
• 化学式: C₁₉H₂₅NO₁₂
• 分子量: 459.407
• InChiKey: MLEHEKGZLUCCDL-DPIHELBLSA-N

物化性质

• 沸点：
  566.3±50.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  170
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  N-acetyl neuraminic acid 、 乙酸酐 生成 5-acetamido-2,4,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosono-1,7-lactone
  参考文献：
  名称：

  SUGIYAMA, NAOKAZU;SUGAI, KEI;YAMADA, NORIYUKI;GOTO, MOTOAKI;BAN, CHIEKO;F+, CHEM. AND PHARM. BULL., 36,(1988) N 3, 1147-1152

  摘要：

  DOI：

文献信息

• Investigation into an efficient synthesis of 2,3-dehydro-N-acetyl neuraminic acid leads to three decarboxylated sialic acid dimers
  作者：Evan J. Horn、Jonel P. Saludes、Jacquelyn Gervay-Hague

  DOI：10.1016/j.carres.2008.01.033

  日期：2008.4

  synthesized in a one-pot reaction by heating peracetylated sialic acid (2) in pyridine and acetic anhydride to induce beta-elimination. When reduced to practice, this reaction produced only modest yields of 4. Six compounds, including three new decarboxylated sialic acid dimers, were also found to have been synthesized in the reaction. In an effort to better understand the chemistry and the mechanisms of

  唾液酸是一种发现于许多生物体细胞表面的重要碳水化合物，现已经过修饰，可广泛用于生物学和制药领域。我们假设通过加热全乙酰化反应可以在一锅反应中高效合成4,7,8,9-四-O-乙酰基-2-脱氧-2,3-脱氢-N-乙酰基神经氨酸甲酯（4）唾液酸（2）在吡啶和乙酸酐中诱导β-消除。当付诸实践时，该反应仅产生适度的产率4。还发现在该反应中已经合成了六种化合物，包括三个新的脱羧唾液酸二聚体。为了更好地理解此反应的化学性质和机理，所有副产物都经过了分离和充分表征。
• Studies on sialic acids. IX. Formation of a 1,7-lactone derivative by direct acetylation of N-acetylneuraminic acid.
  作者：NAOKAZU SUGIYAMA、KEI SUGAI、NORIYUKI YAMADA、MOTOAKI GOTO、CHIEKO BAN、KIMIO FURUHATA、HIROAKI TAKAYANAGI、HARUO OGURA

  DOI：10.1248/cpb.36.1147

  日期：——

  A new lactone compound was isolated as a minor by-product from the reaction mixture of N-acetylneuraminic acid with acetic anhydride in pyridine, in addition to the major product, 2, 4, 7, 8, 9-penta-O-acetyl-N-acetylneuraminic acid. The structure of the new compound was elucidated to be 5-acetamido-2, 4, 8, 9-tetra-O-acetyl-3, 5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosono-1, 7-lactone by nuclear magnetic resonance, mass spectroscopy and X-ray crystal analysis. It was revealed that the absolute configurations of the asymmetric centers of the new compound were consistent with those for the original N-acetylneuraminic acid with the conversion of the pyranose ring conformation from 2C5(D) to 5C2(D).

  除了主要产物 2, 4, 7, 8, 9-五-O-乙酰基-N-乙酰基神经氨酸之外，还从 N-乙酰基神经氨酸与乙酸酐在吡啶中的反应混合物中分离出一种新的内酯化合物作为次要副产品。通过核磁共振、质谱和 X 射线晶体分析，阐明了新化合物的结构为 5-乙酰胺基-2，4，8，9-四-O-乙酰基-3，5-二脱氧-β-D-甘油-D-半乳-2-壬磺吡喃酮-1，7-内酯。结果表明，新化合物不对称中心的绝对构型与原来的 N-乙酰神经氨酸一致，吡喃糖环构象从 2C5(D)转变为 5C2(D)。