1,3,4,6-tetra-O-benzyl-β-D-fructofuranose | 92691-80-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-benzyl-β-D-fructofuranose
• 英文别名: (2R,3S,4R,5R)-3,4-bis(phenylmethoxy)-2,5-bis(phenylmethoxymethyl)oxolan-2-ol
• CAS: 92691-80-0
• 化学式: C₃₄H₃₆O₆
• 分子量: 540.656
• InChiKey: LQAPNUOZMVWFMX-YVEASBDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 1,3,4,6-tetra-O-benzyl-α,β-D-fructofuranoside 在 溶剂黄146 作用下， 反应 2.0h， 生成 1,3,4,6-tetra-O-benzyl-α-D-fructofuranose 、 1,3,4,6-tetra-O-benzyl-β-D-fructofuranose
  参考文献：
  名称：

  Synthesis of D-Fructofuranosylpurine Nucleosides

  摘要：

  The Mitsunobu reaction has been applied to the formation of purine nucleosides of D-fructofuranose. The use of O-benzyl protection results in a predominance of the beta-configuration in these novel compounds and both alpha- and beta-D-fructofuranosyladenine are obtained in stereochemically pure form.

  DOI：

  10.1080/15257779408013257

文献信息

• Preparation of partially benzylated mono-, di-, and trisaccharides by selective cleavage of the β-fructofuranosidic linkage in fully benzylated sucrose and sucrose-related oligosaccharides under acidic conditions
  作者：Takashi Yamanoi、Noriko Misawa、Sho Matsuda、Mikio Watanabe

  DOI：10.1016/j.carres.2008.03.024

  日期：2008.6

  Several partially benzylated mono-, di-, and trisaccharides having an anomeric hydroxyl group were successfully prepared by selective cleavage of the beta-fructofuranosidic linkage in fully benzylated sucrose and sucrose-related oligosaccharides derived from lactosucrose, raffinose, melezitose, stachyose, and nystose under acidic conditions using 1:10 75% aqueous sulfuric acid-dioxane at room temperature

  通过选择性地在完全苄基化的蔗糖和衍生自乳糖蔗糖，棉子糖，松三糖，水苏糖和核糖的蔗糖相关的低聚糖中，β-果糖呋喃糖苷键的选择性裂解，成功制备了具有异头羟基的部分部分苄基化的单糖，二糖和三糖在酸性条件下，使用1:10 75％硫酸-二恶烷水溶液在室温下放置1h。
• Synthesis of D-Fructofuranosylpurine Nucleosides
  作者：Abderrahime Bouali、David F. Ewing、Grahame Mackenzie

  DOI：10.1080/15257779408013257

  日期：1994.3

  The Mitsunobu reaction has been applied to the formation of purine nucleosides of D-fructofuranose. The use of O-benzyl protection results in a predominance of the beta-configuration in these novel compounds and both alpha- and beta-D-fructofuranosyladenine are obtained in stereochemically pure form.