D-mannaro-1,4:6,3-dilactone | 2900-01-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: D-mannaro-1,4:6,3-dilactone
• 英文别名: D-1,4:3,6-mannarodilactone；D-mannaric acid-1=>4;6=>3-dilactone；D-Mannarsaeure-1=>4;6=>3-dilacton；D-Mannarsaeure-1->4;6->3-dilacton；D-Mannosaccharo-1,4,3,6-dilacton；D-Mannarsaeure-1,4:3,6-dilacton；D-Mannaric acid, di-I(3)-lactone；(3S,3aR,6S,6aR)-3,6-dihydroxy-3,3a,6,6a-tetrahydrofuro[3,2-b]furan-2,5-dione
• CAS: 2900-01-8
• 化学式: C₆H₆O₆
• 分子量: 174.11
• InChiKey: QRFNDAVXJCGLFB-ORZLYADOSA-N

物化性质

• 沸点：
  558.6±50.0 °C(Predicted)
• 密度：
  1.892±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-mannaro-1,4:6,3-dilactone 在 sodium hydroxide 、 silver nitrate 作用下， 生成 D-甘露酸
  参考文献：
  名称：

  Rehorst, Chemische Berichte, 1932, vol. 65, p. 1476,1481

  摘要：

  DOI：
• 作为产物：
  描述：

  D-甘露酸 反应 24.0h， 以43.18 g的产率得到D-mannaro-1,4:6,3-dilactone
  参考文献：
  名称：

  d-甘露糖硝酸氧化中的修饰：N，N'-二甲基d-甘露酰胺的X射线晶体结构

  摘要：

  使用计算机控制的反应器在氧气气氛下进行D-甘露糖的硝酸氧化。该方法代表用氧作为末端氧化剂对D-甘露糖的催化氧化。用甲醇的HCl酯化粗氧化产物，然后用甲胺将酯化产物直接转化为结晶的N，N′-二甲基-D-马那酰胺。在氢氧化钠水溶液中处理二酰胺，得到固体D-甘露酸钠。N，N′-二甲基-D-马那酰胺的X射线晶体结构被确定为立体规则聚（亚烷基-D-马那酰胺）的重复D-马那酰胺单元的模型。制备了D-甘露酸钠二酯作为酯化的D-月桂酸的前体，用作反应性二酸单体以制备聚-D-月桂酰胺。

  DOI：

  10.1016/j.carres.2013.05.004

文献信息

• Kiliani, Chemische Berichte, 1930, vol. 63, p. 369,370
  作者：Kiliani

  DOI：——

  日期：——
• Linstead et al., Journal of the Chemical Society, 1953, p. 1211,1216
  作者：Linstead et al.

  DOI：——

  日期：——
• C2-Symmetric inhibitors of Plasmodium falciparum plasmepsin II: synthesis and theoretical predictions
  作者：Karolina Ersmark、Isabella Feierberg、Sinisa Bjelic、Johan Hultén、Bertil Samuelsson、Johan Åqvist、Anders Hallberg

  DOI：10.1016/s0968-0896(03)00339-0

  日期：2003.8

  A series of C-2-symmetric compounds with a mannitol-based scaffold has been investigated, both theoretically and experimentally, as Plm II inhibitors. Four different stereoisomers with either benzyloxy or allyloxy P1/P1' side chains were studied. Computational ranking of the binding affinities of the eight compounds was carried out using the linear interaction energy (LIE) method relying on a complex previously determined by crystallography. Within both series of isomers the theoretical binding energies were in agreement with the enzymatic measurements, illustrating the power of the LIE method for the prediction of ligand affinities prior to synthesis. The structural models of the enzyme-inhibitor complexes obtained from the MD simulations provided a basis for interpretation of further structure-activity relationships. Hence, the affinity of a structurally similar ligand, but with a different P2/P2' substituent was examined using the same procedure. The predicted improvement in binding constant agreed well with experimental results. (C) 2003 Elsevier Ltd. All rights reserved.
• Degradable Thermosets from Sugar-Derived Dilactones
  作者：James J. Gallagher、Marc A. Hillmyer、Theresa M. Reineke

  DOI：10.1021/ma401904x

  日期：2014.1.28

  Using the sugar derivatives glucarodilactone and mannarodilactone, two new dimethacrylate monomers (GDMA and MDMA) were synthesized by a tin-catalyzed alcohol-isocyanate coupling between the dilactones and isocyanatoethyl methacrylate. GDMA was polymerized using thermally initiated free radical polymerization at 135 degrees C in the presence of dicumyl peroxide as an initiator. The fractional conversion of methacrylate groups in PGDMA was determined by FT-IR to be 0.64, within the typical range of poly(dimethacrylates). Tensile testing of PGDMA demonstrated the stiff but brittle nature of this material and the modulus was shown to be similar to that reported for commercially available poly(dimethacrylates) from rigid monomers. The hydrolytic stability of PGDMA was investigated by submersing polymer samples in acidic, neutral, and basic aqueous environments. PGDMA degraded to water-soluble components after 17 days in 1 M NaOH but remained stable under acidic and neutral conditions. Solvent casting a mixture of GDMA, MDMA, and benzoyl peroxide followed by thermal curing at 95 C gave clear P(GDMA-co-MDMA) (3:2) coatings. These coatings showed similar hydrolytic stability to the bulk PGDMA material. GDMA and methyl methacrylate (MMA) were used to synthesize P(GDMA-co-MMA) microspheres by precipitation polymerization in THF. These particles were characterized by dynamic light scattering (DLS) in THF and in the dry state by scanning electron microscopy. Optimization of polymerization conditions yielded 730 nm diameter particles with a spherical morphology and low dispersity as determined by DLS.
• THE ISOLATION AND IDENTIFICATION OF d-MANNURONIC ACID LACTONE FROM THE MACROCYSTIS PYRIFERA
  作者：William L. Nelson、Leonard H. Cretcher

  DOI：10.1021/ja01368a066

  日期：1930.5