Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[12-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylcarbamoyl)-dodecanoylamino]-tetrahydro-pyran-4-yl ester | 208592-24-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[12-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylcarbamoyl)-dodecanoylamino]-tetrahydro-pyran-4-yl ester
• CAS: 208592-24-9
• 化学式: C₄₁H₆₂N₂O₂₀
• 分子量: 902.945
• InChiKey: FBTLSDMHCJPDAW-LOPQOQBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  63.0
• 可旋转键数：
  24.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  287.06
• 氢给体数：
  2.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[12-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylcarbamoyl)-dodecanoylamino]-tetrahydro-pyran-4-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以95%的产率得到N,N'-bis[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]tridecanediamide
  参考文献：
  名称：

  Synthesis of Novel α,ω-Type 1-Glucosamide and 1-Galactosamide Bolaamphiphiles

  摘要：

  A new family of bolaamphiphiles in which two glucosylamine or galactosylamine moieties are linked via a beta-N-glycosidic bond to an alpha,omega-dicarboxylic acid has been described. The 1-D-glucosamide and 1-D-galactosamide bolaamphiphiles were obtained in good yield by the condensation of the dicarboxylic acid dichloride with the corresponding 1-aldopyranosylamine.

  DOI：

  10.1080/07328309808002902
• 作为产物：
  描述：

  十三烷二酸 在 吡啶 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[12-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylcarbamoyl)-dodecanoylamino]-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of Novel α,ω-Type 1-Glucosamide and 1-Galactosamide Bolaamphiphiles

  摘要：

  A new family of bolaamphiphiles in which two glucosylamine or galactosylamine moieties are linked via a beta-N-glycosidic bond to an alpha,omega-dicarboxylic acid has been described. The 1-D-glucosamide and 1-D-galactosamide bolaamphiphiles were obtained in good yield by the condensation of the dicarboxylic acid dichloride with the corresponding 1-aldopyranosylamine.

  DOI：

  10.1080/07328309808002902

文献信息

• Stereochemical Effect of Even−Odd Connecting Links on Supramolecular Assemblies Made of 1-Glucosamide Bolaamphiphiles
  作者：Toshimi Shimizu、Mitsutoshi Masuda

  DOI：10.1021/ja961226y

  日期：1997.3.1

  Bolaamphiphiles with a 1-glucosamide-head group at each end, N,N'-bis(beta-D-glucopyranosyl)alkane-1, n-dicarboxamide [Glc-NC(n)CN-Glc, n=6, 9, 10, 11, 12, 13, and 14], have been synthesized. Self-assembled supramolecular structures in water strongly depend on whether a is even or odd, which respectively give rise to fibrous assemblies or planar platelets as well as amorphous solids. In connection with this even-odd effect of the hydrocarbon links, internal molecular arrangements of the solid fibers were investigated using FT-IR spectroscopy, X-ray diffraction and crystal analyses, and transmission electron microscopy. The oligomethylene groups of the Glc-NC(12)CN-Glc pack in a monoclinic or an orthorhombic mode in the fiber. We propose a possible self-assembled model based on a monolayer sheet, which is stabilized by hydrogen-bond networks via sugar-head and amide groups.
• Non-mesogenic crystal structure of a synthetic 1-d-glucosamide bolaamphiphile
  作者：Mitsutoshi Masuda、Toshimi Shimizu

  DOI：10.1016/s0008-6215(97)00123-7

  日期：1997.8

  The crystal structure of the synthetic 1-glucosamide bolaamphiphile, N,N'-bis(beta-D-glucopyranosyl)undecane-1,11-dicarboxamide (1) was determined by single-crystal X-ray analysis. The space group is P2(1) with cell dimensions: a = 6.220(1), b = 48.25(1), c = 4.922(2) Angstrom, beta = 105.67(2)degrees, and Z = 2. The glucopyranosyl ring is in a C-4(1) chair conformation. The bolaamphiphile molecules are arranged in a layered structure with the alkylene chains packed antiparallel in a pleated sheet. The glucosamine moieties are linked by a three-dimensional intermolecular hydrogen-bonding network. The n-alkylene chain has an all-trans zigzag conformation with a small left-handed twist. (C) 1997 Elsevier Science Ltd.