leucrose (O-α-D-glucopyranosyl-(1-5)-D-fructopyranose) | 58166-26-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: leucrose (O-α-D-glucopyranosyl-(1-5)-D-fructopyranose)
• 英文别名: 5-O-α-D-glucopyranosyl-β-D-fructopyranose；α-D-Glcp-(1->)-D-Fru；β-p-leucrose；D-leucrose；leucrose；α-D-Glcp-(1→5)-D-β-Frup；(2R,3S,4S,5R)-2-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2,3,4-triol
• CAS: 58166-26-0
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: JPFGFRMPGVDDGE-GWRCVIBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  leucrose (O-α-D-glucopyranosyl-(1-5)-D-fructopyranose) 在 吡啶 、 silica gel 、 三氯化铁 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 71.0h， 生成 3,4-di-O-acetyl-1,2-O-isopropylidene-5-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-fructopyranose
  参考文献：
  名称：

  Synthesis and reactions of leucrose and its exocyclic glycal

  摘要：

  5-O-alpha-D-Glucopyranosyl-beta-D-fructopyranose (leucrose, 1) was transformed into 3,4-di-O-acetyl-1-O-methanesulfonyl-5-O-(2,3,4-tri-O-acetyl-6-O-methanes ulfonyl-alpha-D-glucopyranosyl)-beta-D-fructopyranosyl bromide (3) and 1,3,4-tri-O-benzoyl-5-O-(2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl) -beta-D-fructopyranosyl bromide (8), which were converted into derivatives (8 and 9) of 2,6-anhydro-1-deoxy-5-O-alpha-D-glucopyranosyl-D-arabino-hex-1-enitol . Hydrogenation of 8 and 9 gave the corresponding anhydroalditol derivatives. N-Iodosuccinimide-mediated glycosylation of 9 with 1,2,3,4-tetra-O-acetyl-beta-D-glucopyranose gave 1,2,3,4-tetra-O-acetyl-6-O-[3,4-di-O-benzyl-1-deoxy-1-iodo-5-O-(2,3,4,6- tetra-O-benzoyl-alpha-D-glucopyranosyl)-beta-D-fructopyranosyl]- beta-D-glucopyranose (12). Some amino, acetylated, and isopropylidene derivatives of leucrose have been prepared and characterised.

  DOI：

  10.1016/0008-6215(90)80151-r
• 作为产物：
  描述：

  Benzyl-5-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-fructopyranosid 以86%的产率得到
  参考文献：
  名称：

  THIEM, JOACHIM;KLEEBERG, MATTHIAS;KLASKA, KARL-HEINZ, CARBOHYDR. RES., 189,(1989) C. 65-77

  摘要：

  DOI：

文献信息

• Acceptor reactions of alternansucrase from Leuconostoc mesenteroides NRRL B-1355
  作者：Gregory L. Côté、John F. Fobyt

  DOI：10.1016/0008-6215(82)85013-1

  日期：1982.12

  Extracellular glucansucrases from various bacterial sources, including Leuconostoc mesenteroides, have been shown to catalyze the transfer of glucosyl groups from sucrose to low-molecular-weight acceptor sugars, forming a series of oligosaccharides. An extracellular glucansucrase recently isolated from Leuconostoc mesenteroides NRRL B-1355 synthesizes a polysaccharide consisting of alternating α-(1→6)-

  来自各种细菌来源的细胞外葡聚糖蔗糖，包括肠间叶亮葡菌，已显示出可将葡萄糖基团从蔗糖转移至低分子量受体糖，从而形成一系列寡糖。最近从肠膜肠球菌NRNR B-1355中分离出的一种细胞外葡糖苷酶合成了由交替的α-（1→6）-和α-（1→3）连接的d-葡萄糖残基组成的多糖。我们已经发现，在许多低分子量受体糖存在下，这种酶制剂能够形成α-（1→6）-和α-（1→3）-连接的受体产物。d-葡萄糖仅产生异麦芽糖，没有形成黑糖。相似地，甲基α-d-葡萄糖苷，甲基β-d-葡萄糖苷，麦芽糖和黑糖生成了甲基α-异麦芽糖苷，甲基β-异麦芽糖苷，panose和62-O-α-d-葡萄糖基黑麦芽糖，分别。然而，异麦芽糖同时给出了异麦芽三糖和32-O-α-d-葡萄糖基异麦芽糖。这些初始的受体产物也可以充当受体，并且较高dp产物的结构表明，只有当非还原性葡萄糖受体基团通过α-连接时，才形成（1→3）-α-d-糖苷键。 （
• Synthesis of dispirodioxanyl pseudo-oligosaccharides by selective protonic activation of isomeric glycosylfructoses in anhydrous hydrogen fluoride
  作者：Jacques Defaye、José Manuel García Fernández

  DOI：10.1016/0008-6215(94)84273-6

  日期：1994.1

  -beta-D-fructofuranose 1,2':2,1'-dianhydride were respectively obtained, on a preparative scale, by dissolution of the isomeric glycosylfructoses palatinose, leucrose, maltulose, lactulose, and turanose in anhydrous hydrogen fluoride. The reaction, involving selective protonation at the free anomeric position of the fructose unit, was extended to the preparation of the pseudotrisaccharides 6-O-alp

  和无水氟化氢中的杜拉糖。该反应涉及在果糖单元的游离端异构位置处的选择性质子化，扩展到假三糖6-O-α-D-吡喃葡萄糖基-α-D-果糖呋喃糖β-D-果糖基1,2，：2的制备使用tu醛糖和麦芽糖作为二糖前体，从帕拉金糖和果糖中分离出'，1-二酐，以及生成其3-O-，4-O-和4'-O-葡萄糖基类似物。帕拉金糖与麦芽糖和白糖的交叉反应导致制备6-O-α-D-吡喃葡萄糖基-α-D-果糖呋喃糖4-O-α-D-吡喃葡萄糖基-β-D-果糖吡喃糖1,2' ：2,1'-二酐和6-O-α-D-吡喃葡萄糖基-α-D-果糖呋喃糖5-O-α-D-吡喃葡萄糖基-β-D-果糖吡喃糖1,2'：2,1'-二酐分别。该反应涉及在果糖单元的游离端异构位置处的选择性质子化，扩展到假三糖6-O-α-D-吡喃葡萄糖基-α-D-果糖呋喃糖β-D-果糖基1,2，：2的制备使用tu醛糖和麦芽糖作为二糖前体，从帕拉金糖和果糖中分离出'，1-
• Selective protonic activation of isomeric glycosylfructoseswith pyridinium poly(hydrogen fluoride) and synthesis of spirodioxanyl oligosaccharides
  作者：Jacques Defaye、José Manuel Garcia Fernández

  DOI：10.1016/s0008-6215(92)84246-o

  日期：1992.12

  Selective activation of the ketose unit in the isomeric glycosylfructoses, palatinose, leucrose, maltulose, turanose and lactulose, with pyridinium poly(hydrogen fluoride) resulted in the almost quantitative formation of glycosylated difructose dianhydrides. The reaction preferentially involves a reactive fructofuranosyl oxocarbenium ion and is subject to stereoelectronic control. The relative amounts

  用吡啶鎓聚（氟化氢）选择性活化糖基果糖异构酶，帕拉金糖，白糖，麦芽糖，杜兰糖和乳果糖中的酮糖单元，导致几乎定量地形成糖基化的二果糖二酐。该反应优选涉及反应性的呋喃呋喃糖基氧代碳鎓离子，并进行立体电子控制。一系列中获得的异构体螺二恶烷基寡糖的相对量显示出取决于反应条件，尤其是取决于氟化氢与吡啶之比。使用吡啶中合适浓度的氟化氢，将反应容易地引导至动力学二呋喃糖基或热力学吡喃糖基衍生物的形成。
• The formation of novel saccharinic acids, 2-C-(2-hydroxyethyl)tetronic acids, by alkaline degradation of leucrose
  作者：K Niemelä

  DOI：10.1016/0008-6215(96)00041-9

  日期：1996.5.14
• THIEM, JOACHIM;KLEEBERG, MATTHIAS, CARBOHYDR. RES., 205,(1990) C. 333-345
  作者：THIEM, JOACHIM、KLEEBERG, MATTHIAS

  DOI：——

  日期：——