3,4-di-O-benzyl-L-arabinopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-di-O-benzyl-L-arabinopyranose
• 英文别名: 3,6-di-O-benzyl-L-arabinopyranose；(3R,4R,5S)-4,5-bis(phenylmethoxy)oxane-2,3-diol
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: AEZAFYBFOKWMDJ-TUVJXNFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-di-O-benzyl-L-arabinopyranose 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以90%的产率得到3,4-di-O-benzyl-L-arabitol
  参考文献：
  名称：

  Synthesis of Anemoclemoside B, the First Natural Product with an Open-Chain Cyclic Acetal Glycosidic Linkage

  摘要：

  [GRAPHICS]Anemoclemoside B (1), the first natural product containing a brand-new glycosidic linkage, the open-chain cyclic acetal linkage, was synthesized.

  DOI：

  10.1021/ol050324y

文献信息

• Ring-Contraction vs Ring-Expansion Reactions of Spiro-cyclopropanecarboxylated Sugars
  作者：Bandi Ramakrishna、Perali Ramu Sridhar

  DOI：10.1021/ol402021e

  日期：2013.9.6

  Electrophilic ring opening of spiro-cyclopropanecarboxylated sugars followed by reaction with DBU revealed interesting ring-contraction and ring-expansion reactions depending on the substrate and the kind of hydroxyl protective group present adjacent to the Spiro center. A stereoselective method for accessing a new class of carbon chain extended keto-furanoses and C-glycosylated bicyclic compounds is reported.
• Synthesis of Anemoclemoside B, the First Natural Product with an Open-Chain Cyclic Acetal Glycosidic Linkage
  作者：Jiansong Sun、Xiuwen Han、Biao Yu

  DOI：10.1021/ol050324y

  日期：2005.5.1

  [GRAPHICS]Anemoclemoside B (1), the first natural product containing a brand-new glycosidic linkage, the open-chain cyclic acetal linkage, was synthesized.