methyl 1,3-O-benzylidene-α-L-sorbopyranoside | 1025096-34-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: methyl 1,3-O-benzylidene-α-L-sorbopyranoside
• 英文别名: Methyl-1,3-O-benzyliden-α-L-psicopyranosid
• CAS: 1025096-34-7
• 化学式: C₁₄H₁₈O₆
• 分子量: 282.293
• InChiKey: YPIRHGDZMDXUSC-MEBFFEOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 1,3-O-benzylidene-α-L-sorbopyranoside 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 barium carbonate 、 potassium thioacetate 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 methyl 1,5-anhydro-3-O-benzoyl-4-O-mesyl-1-thio-β-D-fructopyranoside
  参考文献：
  名称：

  Preparation of Anhydro-Thiohexopyranosides and -Thiohexofuranosides with D-fructo-, L-sorbo-, L-psico- and L-tagato-Configuration Starting from L-Sorbose

  摘要：

  Methyl alpha- L-sorbopyranoside is transformed into the bicyclic thiosugar methyl 1,5-anhydro-3,4-di-O-mesyl-1-thio-beta-D-fructopyranoside in two steps, whereas the corresponding 3-O-benzoate is obtained from methyl 1,3-O-benzylidene-alpha-L-sorbopyranoside in three steps. 2,3-O-Isopropylidenesorbofuranosides, on the other hand, can be transformed into 6-S-thioacetates by use of the thio-Mitsunobu reaction. These are suitable precursors for the preparation of 1,6-anhydro-1-thiosorbofuranosides. Also, methyl 1-S-acetyl-1-thio-L-sorbofuranosides with mesylate leaving groups are available by the thio-Mitsunobu reaction. They yield 1,4-anhydro-1-thio-beta-L-tagatofuranosides, 1,3-anhydro-alpha-L-psicofuranosides and 1,6-anhydro-1-thio-alpha-L-sorbofuranosides depending on the configuration of the starting compound. Attempts to prepare azido-thio-sugars by displacement of mesylate groups with alkali metal azides failed.

  DOI：

  10.1080/10426500701340915
• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 methyl α-L-sorbopyranoside 在 camphor-10-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以57%的产率得到methyl 1,3-O-benzylidene-α-L-sorbopyranoside
  参考文献：
  名称：

  Preparation of Anhydro-Thiohexopyranosides and -Thiohexofuranosides with D-fructo-, L-sorbo-, L-psico- and L-tagato-Configuration Starting from L-Sorbose

  摘要：

  Methyl alpha- L-sorbopyranoside is transformed into the bicyclic thiosugar methyl 1,5-anhydro-3,4-di-O-mesyl-1-thio-beta-D-fructopyranoside in two steps, whereas the corresponding 3-O-benzoate is obtained from methyl 1,3-O-benzylidene-alpha-L-sorbopyranoside in three steps. 2,3-O-Isopropylidenesorbofuranosides, on the other hand, can be transformed into 6-S-thioacetates by use of the thio-Mitsunobu reaction. These are suitable precursors for the preparation of 1,6-anhydro-1-thiosorbofuranosides. Also, methyl 1-S-acetyl-1-thio-L-sorbofuranosides with mesylate leaving groups are available by the thio-Mitsunobu reaction. They yield 1,4-anhydro-1-thio-beta-L-tagatofuranosides, 1,3-anhydro-alpha-L-psicofuranosides and 1,6-anhydro-1-thio-alpha-L-sorbofuranosides depending on the configuration of the starting compound. Attempts to prepare azido-thio-sugars by displacement of mesylate groups with alkali metal azides failed.

  DOI：

  10.1080/10426500701340915

文献信息

• A Direct Method for the Efficient Synthesis of Benzylidene Acetal at Room Temperature
  作者：Narra Rajashekar Reddy、Rashmi Kumar、Sundarababu Baskaran

  DOI：10.1002/ejoc.201801731

  日期：2019.2.21

  developed for the efficient synthesis of benzylidene acetal from aldehyde at room temperature. In this metal‐free method, Cl3CCN serves as a water scavenger as well as reaction medium and the acid catalyst is readily recovered and recycled. At room temperature, a wide variety of aryl and α,β‐unsaturated aldehydes react readily with functionalized diols and optically active diols to furnish the corresponding

  已经开发出一种简单而直接的方法，用于在室温下从醛中高效合成亚苄基乙缩醛。在这种无金属方法中，Cl 3 CCN可用作除水剂和反应介质，并且酸催化剂易于回收和再循环。在室温下，各种各样的芳基和α，β-不饱和醛容易与官能化的二醇和旋光性二醇反应，以很高的收率提供相应的缩醛。几个敏感的官能团在反应条件下是稳定的。