benzyl β-D-fructofuranoside | 76867-26-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl β-D-fructofuranoside
• 英文别名: benzyl-β-D-fructofuranoside
• CAS: 76867-26-0
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: DSPWXZNLYDTKRN-FVCCEPFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.0
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  99.38
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl β-D-fructofuranoside 在 5 beads of Amberlite IR-120(H+) 作用下， 以 水 为溶剂， 反应 0.5h， 生成 D-fructose
  参考文献：
  名称：

  二甲基亚砜溶液中蔗糖的热解

  摘要：

  摘要研究了无水二甲基亚砜中蔗糖在溶液中的热分解动力学。分子内氢键似乎促进了该反应，而分子间氢键与水或醇的反应则抑制了该反应。热解产生α-d-葡糖吡喃糖（然后发生异构化）和果糖呋喃糖基碳离子，其可以与苯甲醇反应以产生苄基α-和β-d-果糖呋喃糖苷。果糖基阳离子可能也是蔗糖热解中形成2，6-脱水果糖呋喃糖的前体。

  DOI：

  10.1016/s0008-6215(00)85207-6
• 作为产物：
  描述：

  苯甲醇 、 蔗糖 在 Bacillus subtilis levansucrase 作用下， 生成 benzyl β-D-fructofuranoside
  参考文献：
  名称：

  Enzymatic fructosylation of aromatic and aliphatic alcohols by Bacillus subtilis levansucrase: Reactivity of acceptors

  摘要：

  Levansucrases from Bacillus subtilis (BS-LVS) and Leuconostoc mesenteroides ssp. mesenteroides ATCC 8293 (LevC), inulosucrase from Leuconostoc citreum (IslA) and an invertase from Saccharomyces cerevisiae (Inv) were evaluated in acceptor reactions with non-sugar acceptors. Among them, BS-LVS was selected for the fructosylation of aromatic or aliphatic alcohols due to its high activity and stability. The effects of acceptor concentration, enzyme concentration and the presence of a co-solvent in the fructosylation efficiency of hydroquinone were evaluated. It was demonstrated that this reaction is kinetically controlled, producing the best yields of phenolic fructosides when 500 mM of acceptor and 5 U mL(-1) of enzyme were employed. Higher enzyme loads resulted in the rapid hydrolysis of the products. Increased amounts of organic co-solvent up to 50% (v/v) reduced fructoside yield due to a concomitant decrease in the thermodynamic activity of the acceptor, as confirmed by theoretical calculations using COSMO-RS; moreover, increased fructose transfer to levan and reduced hydrolysis were observed. It was found that BS-LVS preferentially fructosylates aromatic over aliphatic alcohols. A maximum fructoside production (19-35 mM) was obtained with dihydroxybenzene acceptors such as hydroquinone, whereas reactions with primary alcohols, such as benzyl alcohol resulted in lower fructosylation efficiency. This selectivity was also demonstrated by the fact that 4-hydroxybenzylalcohol, a bifunctional acceptor, was fructosylated at a rate ten times faster on its aromatic hydroxyl group. BS-LVS selectivity over phenol fructosylation was inversely correlated with the acceptor pK(a) value. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.02.002

文献信息

• Formation and equilibration of d-fructosides and 2-thio-d-fructosides in acidified dimethyl sulfoxide: synthetic and mechanistic aspects
  作者：Wayne Moody、Geoffrey N. Richards

  DOI：10.1016/0008-6215(83)88456-0

  日期：1983.12

  -fructosides is discussed, and some tentative conclusions have been reached on the mechanisms of their furanoside-pyranoside equilibration. The change in ring size in such systems probably proceeds via an anhydro- d -fructose intermediate, rather than an acyclic intermediate. The synthetic applications of the system have been explored, and it has been shown that both d -fructosides and 2-thio- d -fructosides

  摘要报道了在稀酸催化下，酮糖和酮苷反应生成酮基碳鎓离子的动力学研究，并研究了该离子与醇和硫醇亲核试剂的后续反应。讨论了d-果糖苷和2-硫代-d-果糖苷的相对反应性，并就呋喃糖苷-吡喃糖苷平衡的机理得出了一些初步结论。在这样的系统中，环大小的改变可能是通过脱水果糖中间体而不是无环中间体进行的。已经探索了该系统的合成应用，并且已经表明，可以高收率合成d-果糖苷和2-硫代-d-果糖苷。d-果糖呋喃糖苷最好以蔗糖为原料获得，而吡喃糖苷是通过使用所需的醇或硫醇从任何容易获得的d-果糖吡喃糖苷（例如，甲基β）中获得的，仅获得β端基异构体。报道了三种新的2-硫代-d-果糖苷。
• Thermolysis of sucrose in the presence of alcohols. A novel method for the synthesis of d-fructofuranosides
  作者：Wayne Moody、Geoffrey N. Richards

  DOI：10.1016/s0008-6215(00)80670-9

  日期：1981.11

  sucrose is thermolyzed in the presence of alcohols, either neat or in dimethyl sulfoxide solution, the products are mainly d -glucose and the appropriate alkyl d -fructofuranosides. Conditions have been investigated for optimizing the yields of the latter products, with a view to utilization of the reaction as a synthetic method. Such sterically hindered alcohols as 2-methyl-2-propanol and three sterols

  摘要蔗糖在纯醇或二甲基亚砜溶液中在醇存在下进行热解时，产物主要为d-葡萄糖和适当的烷基d-果糖呋喃糖苷。为了将反应用作合成方法，已经研究了用于优化后一种产物的产率的条件。诸如2-甲基-2-丙醇之类的空间受阻醇和三种甾醇不易参与反应。苯酚似乎发生了反应，但是苯基d-果糖呋喃糖苷可能随后被降解，从而提高了2,6-脱水-d-果糖呋喃糖的产量。