(2S,4R,5R,6S)-4-<(1R)-1,2-dihydroxyethyl>-5-hydroxy-6-hydroxymethyl-2-phenyl-1,3-dioxane | 61340-09-8

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (2S,4R,5R,6S)-4-<(1R)-1,2-dihydroxyethyl>-5-hydroxy-6-hydroxymethyl-2-phenyl-1,3-dioxane
• 英文别名: 2,4-O-benzylidene-D-sorbitol；O²,O⁴-((S)-benzylidene)-D-glucitol；O²,O⁴-((S)-Benzyliden)-D-glucit；(R)-1-((2S,4R,5R,6S)-5-Hydroxy-6-(hydroxymethyl)-2-phenyl-1,3-dioxan-4-yl)ethane-1,2-diol；(1R)-1-[(2S,4R,5R,6S)-5-hydroxy-6-(hydroxymethyl)-2-phenyl-1,3-dioxan-4-yl]ethane-1,2-diol
• CAS: 61340-09-8
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: UZTHQPNUYCELPZ-MLGHIDQZSA-N

物化性质

• 沸点：
  546.6±45.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4R,5R,6S)-4-<(1R)-1,2-dihydroxyethyl>-5-hydroxy-6-hydroxymethyl-2-phenyl-1,3-dioxane 在 copper(II) sulfate 、 丙酮 作用下， 生成 O²,O⁴-((S)-benzylidene)-O⁵,O⁶-isopropylidene-D-glucitol
  参考文献：
  名称：

  v. Vargha, Chemische Berichte, 1935, vol. 68, p. 18,22

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 、 溶剂黄146 作用下， 生成 (2S,4R,5R,6S)-4-<(1R)-1,2-dihydroxyethyl>-5-hydroxy-6-hydroxymethyl-2-phenyl-1,3-dioxane
  参考文献：
  名称：

  1,3:2,4-Dibenzylidene-D-sorbitol

  摘要：

  DOI：

  10.1021/ja01233a501

文献信息

• Stereoselective formation of tetrahydrofurans during allyltrimethylsilane additions to L-xylose derivatives
  作者：Ronald A. Veloo、Martin J. Wanner、Gerrit-Jan Koomen

  DOI：10.1016/s0040-4020(01)89027-x

  日期：——

  Stereoselective addition reactions to the aldehyde function of some L-xylose derivatives, under the influence of Lewis acid catalysts, lead to the formation of tetrahydrofuran derivatives at low temperatures, depending on the acetal protecting groups used. Via separate reactions it was shown, that these tetrahydrofurans seemed to be intermediates in the formation of homoallyl alcohols.

  在路易斯酸催化剂的影响下，对一些L-木糖衍生物的醛官能团的立体选择性加成反应导致在低温下形成四氢呋喃衍生物，具体取决于所用的缩醛保护基。通过单独的反应表明，这些四氢呋喃似乎是形成均烯丙基醇的中间体。
• Thermal and Rheological Properties of Physical Gels Formed from Benzylidene-D-sorbitol Derivatives
  作者：Mineo Watase、Hideyuki Itagaki

  DOI：10.1246/bcsj.71.1457

  日期：1998.6

  The thermal and rheological properties of gels formed from 2,4-(mono)-O-benzylidene-d-sorbitol (MBS), 1,3 : 2,4-di-O-benzylidene-d-sorbitol (DBS), and 1,3 : 2,4 : 5,6-tri-O-benzylidene-d-sorbitol (TBS) in ethylene glycol (EG) and from DBS in glycerol (GL) were investigated. In all the gels studied, the values of the enthalpy of melting for the gel obtained from the Eldridge–Ferry plot agreed well with those obtained from the peak area of the DSC curves. This agreement has not been demonstrated clearly for biopolymeric systems thus far but can now be successfully shown by first using small molecule systems. In conclusion, the transitions of the gel formation and gel melting proceed via a second order or higher order process. The experimental results show that the ease by which formation and stabilization of gels takes place for the sorbitol derivatives in EG is in the following order: DBS > TBS > MBS. Accordingly, the main reason for the stabilization of sorbitol gels in alcoholic solvents is concluded to be not simply due to hydrogen bonding or hydrophobic interactions among benzylidene groups but rather it is due to a delicate balance of chemical structure that facilitates the formation of crystals. In particular, the symmetric structure of a DBS molecule, which has a rigid and chiral ten-member ring symmetrically connected with two benzylidene groups in equatorial positions, is considered to be the most crucial reason to form most stable gels studied in this work.

  研究了乙二醇（EG）中的 2,4-（单）-O-亚苄基-d-山梨糖醇（MBS）、1,3 : 2,4-二-O-亚苄基-d-山梨糖醇（DBS）、1,3 : 2,4 : 5,6-三-O-亚苄基-d-山梨糖醇（TBS）以及甘油（GL）中的 DBS 所形成的凝胶的热学和流变学特性。在所研究的所有凝胶中，根据埃尔德里奇-费里曲线图得出的凝胶熔化焓值与根据 DSC 曲线峰面积得出的凝胶熔化焓值非常吻合。迄今为止，这种一致性尚未在生物聚合物体系中得到明确证明，但现在可以通过首先使用小分子体系来成功证明。总之，凝胶形成和凝胶熔化的转变是通过二阶或高阶过程进行的。实验结果表明，山梨醇衍生物在 EG 中形成和稳定凝胶的难易程度按以下顺序排列：DBS > TBS > MBS。因此，可以断定山梨醇凝胶在酒精溶剂中稳定的主要原因并不仅仅是苯亚甲基之间的氢键或疏水作用，而是化学结构的微妙平衡促进了晶体的形成。特别是 DBS 分子的对称结构，它有一个刚性的手性十元环，在赤道位置对称地连接着两个亚苄基，这被认为是形成本研究中最稳定凝胶的最关键原因。
• Bourne et al., Journal of the Chemical Society, 1959, p. 1864,1869
  作者：Bourne et al.

  DOI：——

  日期：——
• Micheel; Hasse, Chemische Berichte, 1935, vol. 68, p. 1582,1584
  作者：Micheel、Hasse

  DOI：——

  日期：——
• v. Vargha, Chemische Berichte, 1935, vol. 68, p. 1377,1378
  作者：v. Vargha

  DOI：——

  日期：——