(4S,5S)-2-tert-butyl-4,5-dihydroxymethyl-2-methyldioxolane | 492447-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5S)-2-tert-butyl-4,5-dihydroxymethyl-2-methyldioxolane
• 英文别名: [(4S,5S)-2-tert-butyl-5-(hydroxymethyl)-2-methyl-1,3-dioxolan-4-yl]methanol
• CAS: 492447-17-3
• 化学式: C₁₀H₂₀O₄
• 分子量: 204.266
• InChiKey: QBEZMVAFAVJQQP-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四乙二醇二对甲苯磺酸酯 、 (4S,5S)-2-tert-butyl-4,5-dihydroxymethyl-2-methyldioxolane 在 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 17.0h， 以67%的产率得到(3aS,18aS)-2-(tert-butyl)-2-methyldodecahydro[1,3]dioxolo[4,5-o][1,4,7,10,13]pentaoxacycloheptadecane
  参考文献：
  名称：

  摘要：

  Condensation of (4S,5S)-4,5-dihydroxymethyl-2-substituted dioxolanes with polyethylene glycols ditosylates yielded new chiral crown ethers. By potentiometry the enantioselectivity of complexing between the compounds obtained and L- and D-valine methyl ester hydrochlorides was evaluated.

  DOI：

  10.1023/a:1020315910332
• 作为产物：
  描述：

  diethyl (4R,5R)-2-tert-butyl-2-methyl-1,3-dioxolane-4,5-dicarboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以79%的产率得到(4S,5S)-2-tert-butyl-4,5-dihydroxymethyl-2-methyldioxolane
  参考文献：
  名称：

  摘要：

  Condensation of (4S,5S)-4,5-dihydroxymethyl-2-substituted dioxolanes with polyethylene glycols ditosylates yielded new chiral crown ethers. By potentiometry the enantioselectivity of complexing between the compounds obtained and L- and D-valine methyl ester hydrochlorides was evaluated.

  DOI：

  10.1023/a:1020315910332

文献信息

• Synthesis and Enantiodifferentiating Properties of Chiral Aza Crown Ethers
  作者：A. V. Lobach、O. N. Leus、N. Yu. Titova、N. G. Luk'yanenko

  DOI：10.1023/b:rujo.0000003200.41968.46

  日期：2003.7

  Alkylation of 2-substituted (4S,5S)-4,5-bis(hydroxymethyl)-1,3-dioxolanes with 9-benzyl-1,17-di-iodo-3,6,12,15-tetraoxa-9-azaheptadecane afforded new chiral aza and diaza crown ethers as a result of [1+1] and [2+2] additions. Their catalytic debenzylation gave the corresponding derivatives with a secondary amino group. The reaction of diethyl (+)-tartrate and diethyl (4S,5S)-1,3-dioxolane-4,5-diacetates with 1,8-diamino-3,6-dioxaoctane led to formation of chiral macrocyclic lactams which were reduced with lithium aluminum hydride. The resulting diaza crown ethers were tested for enantioselectivity in complex formation with L- and D-valine methyl ester by the potentiometric method. In most cases, the aza crown ethers showed better enantioselectivity than their oxygen analogs.
• ——
  作者：N. G. Luk'yanenko、A. V. Lobach、O. N. Leus、N. Yu. Titova

  DOI：10.1023/a:1020315910332

  日期：——

  Condensation of (4S,5S)-4,5-dihydroxymethyl-2-substituted dioxolanes with polyethylene glycols ditosylates yielded new chiral crown ethers. By potentiometry the enantioselectivity of complexing between the compounds obtained and L- and D-valine methyl ester hydrochlorides was evaluated.