(2S,3R,4R,5R)-ethyl-5-((1S,2R)-1,2-dihydroxy-3-(trityloxy)propyl)-2,4-dihydroxy-2-methyltetrahydrofuran-3-carboxylate | 1430215-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2S,3R,4R,5R)-ethyl-5-((1S,2R)-1,2-dihydroxy-3-(trityloxy)propyl)-2,4-dihydroxy-2-methyltetrahydrofuran-3-carboxylate
• CAS: 1430215-33-0
• 化学式: C₃₀H₃₄O₈
• 分子量: 522.595
• InChiKey: MPLSKSZMOLBSJG-VYTOZGFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  125.68
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  (3S,4R,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,3,4-triol 、 乙酰乙酸乙酯 在 2-羟基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 以14%的产率得到(2R,3S,4S,5R,6R)-ethyl-2,4,5-trihydroxy-6-((S)-1-hydroxy-2-(trityloxy)ethyl)-2-methyltetrahydro-2H-pyran-3-carboxylate
  参考文献：
  名称：

  Organocatalyzed Knoevenagel-addition—simple access to carbon chain-elongated branched carbohydrates

  摘要：

  Chain elongations of unprotected carbohydrates via a Knoevenagel-addition are described. The reactions were carried out in the presence of catalytic amounts of tertiary amines. The C-C bond formation processes yielded high syn-stereoselectivities. Additionally, through an asymmetric induction controlled by the configuration of the deployed carbohydrates pyranoid or furanoid products were formed. Yields were strongly increased by the use of 5-protected carbohydrates in these transformations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.063