[(4S)-1-methoxy-3,4-dihydro-1H-isochromen-4-yl] acetate | 862288-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: [(4S)-1-methoxy-3,4-dihydro-1H-isochromen-4-yl] acetate
• CAS: 862288-39-9
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: VSAWVEJFEHDUBV-JHJMLUEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(4S)-1-methoxy-3,4-dihydro-1H-isochromen-4-yl] acetate 在 甲醇 、 氨 、 tin(ll) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 1-((1S,4S)-4-Hydroxy-isochroman-1-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Asymmetric synthesis of thymine nucleoside analogues based on the isochroman core

  摘要：

  Diastereoisomeric analogues of d4T having an isochroman core as the glycone moiety have been prepared in seven steps. Starting from phthalaldehyde, two chiral centres analogous to the alpha/beta anomers of D/L sugars were created. The first was obtained enantiomerically pure via asymmetric dihydroxylation and the second via cyclisation of an aldehyde group with a primary hydroxyl group. Retention of chiral integrity at the C-4 Site enabled enantiomerically pure nucleoside analogues to be obtained. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.091
• 作为产物：
  描述：

  邻苯二甲醛 在 盐酸 、 AD-mix-α 、 正丁基锂 、 对甲苯磺酸 、 叔丁醇 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 [(4S)-1-methoxy-3,4-dihydro-1H-isochromen-4-yl] acetate
  参考文献：
  名称：

  Asymmetric synthesis of thymine nucleoside analogues based on the isochroman core

  摘要：

  Diastereoisomeric analogues of d4T having an isochroman core as the glycone moiety have been prepared in seven steps. Starting from phthalaldehyde, two chiral centres analogous to the alpha/beta anomers of D/L sugars were created. The first was obtained enantiomerically pure via asymmetric dihydroxylation and the second via cyclisation of an aldehyde group with a primary hydroxyl group. Retention of chiral integrity at the C-4 Site enabled enantiomerically pure nucleoside analogues to be obtained. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.091