ethyl-(5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-D-xylo-heptofuranosid)uronate | 302801-27-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl-(5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-D-xylo-heptofuranosid)uronate
• 英文别名: ethyl 3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propanoate
• CAS: 302801-27-0
• 化学式: C₁₃H₂₂O₆
• 分子量: 274.314
• InChiKey: PGBBSDRRVVHGMX-SASUGWTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl-(5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-D-xylo-heptofuranosid)uronate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以97%的产率得到5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-D-xylofuranosiduronic acid
  参考文献：
  名称：

  An Olefin Metathesis Route for the Preparation of (1→6)-Linked C-Disaccharide Glycals. A Convergent and Flexible Approach to C-Saccharide Synthesis

  摘要：

  A convergent route to a variety of C-1-disaccharide glycals based on the olefin metathesis reaction of enol ethers and alkenes is described. The DCC-mediated coupling reaction of a variety of pentose enitols (la-c) with a number of C-5- and C-6-monosaccharide carboxylic acids (2a-e) gave the corresponding esters 3a-1 in good yield. Methylenation of these compounds was followed by ring-closing metathesis, mediated by the Schrock molybdenum catalyst 8 in warm toluene, to provide the target C-disaccharide glycals 5a-1. The formed enol ether double bond in 5a was then transformed, via standard manipulations, into a variety of C-disaccharide derivatives 21-25.

  DOI：

  10.1021/jo0005159
• 作为产物：
  描述：

  ((3aR,5R,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methanol 在 palladium on activated charcoal swern reagent 、 氢气 作用下， 以 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 、 苯 为溶剂， -78.0~20.0 ℃ 、241.32 kPa 条件下， 生成 ethyl-(5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-D-xylo-heptofuranosid)uronate
  参考文献：
  名称：

  An Olefin Metathesis Route for the Preparation of (1→6)-Linked C-Disaccharide Glycals. A Convergent and Flexible Approach to C-Saccharide Synthesis

  摘要：

  A convergent route to a variety of C-1-disaccharide glycals based on the olefin metathesis reaction of enol ethers and alkenes is described. The DCC-mediated coupling reaction of a variety of pentose enitols (la-c) with a number of C-5- and C-6-monosaccharide carboxylic acids (2a-e) gave the corresponding esters 3a-1 in good yield. Methylenation of these compounds was followed by ring-closing metathesis, mediated by the Schrock molybdenum catalyst 8 in warm toluene, to provide the target C-disaccharide glycals 5a-1. The formed enol ether double bond in 5a was then transformed, via standard manipulations, into a variety of C-disaccharide derivatives 21-25.

  DOI：

  10.1021/jo0005159