(2R,3S,4S,5S,6S)-ethyl 6-((R)-1,2-dihydroxyethyl)-2,4,5-trihydroxy-2-methyltetra-hydro-2H-pyran-3-carboxylate | 1376461-43-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2R,3S,4S,5S,6S)-ethyl 6-((R)-1,2-dihydroxyethyl)-2,4,5-trihydroxy-2-methyltetra-hydro-2H-pyran-3-carboxylate
• CAS: 1376461-43-6
• 化学式: C₁₁H₂₀O₈
• 分子量: 280.275
• InChiKey: WWSZCFFZNURWGT-YGAQGDHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.65
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  136.68
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  异恶唑，3-isocyanato-5-(1-methylethyl)-(9CI) 、 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， 生成 (2R,3S,4S,5S,6S)-ethyl 6-((R)-1,2-dihydroxyethyl)-2,4,5-trihydroxy-2-methyltetra-hydro-2H-pyran-3-carboxylate 、 (2S,3R,4R,5S)-ethyl-2,4-dihydroxy-2-methyl-5-((1S,2R)-1,2,3-trihydroxypropyl)-tetrahydrofuran-3-carboxylate
  参考文献：
  名称：

  Stereoselective amine-catalyzed carbohydrate chain elongation

  摘要：

  未受保护的碳水化合物与1,3-二羰基化合物的羟醛加成已被描述。该转化基于叔胺和 2-羟基吡啶的双重活化。

  DOI：

  10.1039/c2cc31541f

文献信息

• Organocatalyzed Knoevenagel-addition—simple access to carbon chain-elongated branched carbohydrates
  作者：Benjamin Voigt、Anastassia Matviitsuk、Rainer Mahrwald

  DOI：10.1016/j.tet.2013.03.063

  日期：2013.5

  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.