5-acetamido-3,5-dideoxy-2-O-methyl-D-glycero-D-galacto-2-noneno-1,4-lactone | 115400-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 5-acetamido-3,5-dideoxy-2-O-methyl-D-glycero-D-galacto-2-noneno-1,4-lactone
• 英文别名: 5-acetamido-2-O-methyl-3,5-dideoxy-D-glycero-D-galacto-2-noneno-1,4-lactone；N-[(1S,2R,3S,4R)-2,3,4,5-tetrahydroxy-1-[(2S)-4-methoxy-5-oxo-2H-furan-2-yl]pentyl]acetamide
• CAS: 115400-39-0
• 化学式: C₁₂H₁₉NO₈
• 分子量: 305.285
• InChiKey: LBJYYFZOBYSLFQ-XKLWRSMXSA-N

物化性质

• 沸点：
  778.1±60.0 °C(predicted)
• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-acetamido-3,5-dideoxy-2-O-methyl-D-glycero-D-galacto-2-noneno-1,4-lactone 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  γ-内酯型唾液酸的合成，是2，3-脱氢唾液酸的异构体。

  摘要：

  由相应的唾液酸酯有效地合成了γ-内酯型唾液酸，它是2，3-脱氢唾液酸的异构体。从γ-内酯重建唾液酸酯，产率为95％。γ-内酯结构是通过甲基化为相应的甲基醚来确定的。

  DOI：

  10.1271/bbb.90912
• 作为产物：
  描述：

  N-acetyl neuraminic acid 在 sodium methylate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.0h， 生成 5-acetamido-3,5-dideoxy-2-O-methyl-D-glycero-D-galacto-2-noneno-1,4-lactone
  参考文献：
  名称：

  γ-内酯型唾液酸的合成，是2，3-脱氢唾液酸的异构体。

  摘要：

  由相应的唾液酸酯有效地合成了γ-内酯型唾液酸，它是2，3-脱氢唾液酸的异构体。从γ-内酯重建唾液酸酯，产率为95％。γ-内酯结构是通过甲基化为相应的甲基醚来确定的。

  DOI：

  10.1271/bbb.90912

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%。
• Studies on sialic acids. VIII. The 1,4-lactone derivatives of N-acetylneuraminic acid.
  作者：KIMIO FURUHATA、SHINGO SATO、KATSUKO ANAZAWA、MOTOAKI GOTO、HIROAKI TAKAYANAGI、HARUO OGURA

  DOI：10.1248/cpb.35.3609

  日期：——

  The reactions of N-acetylneuraminic acid with benzyl, allyl, and methyl halides in the presence of excess cesium carbonate gave the corresponding N-acetyl-2-O-alkyl-3, 5-dideoxy-D-glycero-D-galacto-2-noneno-1, 4-lactones in good yields. The structures and stereochemistry of these 1, 4-lactonic sialic acid derivatives were elucidated from the infrared and proton nuclear magnetic resonance spectra and by X-ray crystal analysis.

  在碳酸铯过量的情况下，N-乙酰神经氨酸与苄基、烯丙基和甲基卤化物的反应，产生了相应的N-乙酰-2-O-烷基-3,5-二脱氧-D-甘油-D-半乳糖-2-壬烯-1,4-内酯，且产量良好。通过红外光谱、质子核磁共振光谱和X射线晶体分析，阐明了这些1,4-内酯唾液酸衍生物的结构和立体化学。
• Synthesis of γ-Lactone-Type Sialic Acid, an Isomer of 2,3-Dehydrosialic Acid
  作者：Yoshiharu SAWADA、Shin-ichi NAKATSUKA

  DOI：10.1271/bbb.90912

  日期：2010.5.23

  An efficient synthesis of gamma-lactone-type sialic acid, which is an isomer of 2,3-dehydrosialic acid, was achieved from the corresponding sialic ester. The sialic ester was reconstructed from the gamma-lactone in a 95% yield. The gamma-lactone structure was determined by methylating to its corresponding methyl ether.

  由相应的唾液酸酯有效地合成了γ-内酯型唾液酸，它是2，3-脱氢唾液酸的异构体。从γ-内酯重建唾液酸酯，产率为95％。γ-内酯结构是通过甲基化为相应的甲基醚来确定的。