ethyl (2S,4S,6R)-4-hydroxy-6-methyloxane-2-carboxylate | 1187319-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: ethyl (2S,4S,6R)-4-hydroxy-6-methyloxane-2-carboxylate
• CAS: 1187319-57-8
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: OHPXPVQCDOBGAH-CSMHCCOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.48
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl (2S,4S,6R)-4-hydroxy-6-methyloxane-2-carboxylate 、 三氟甲烷磺酸甲酯 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 4.5h， 以35%的产率得到ethyl (2S,4S,6R)-4-methoxy-6-methyltetrahydro-2H-pyran-2-carboxylate
  参考文献：
  名称：

  Chiral Phosphoric Acid-Governed Anti-Diastereoselective and Enantioselective Hetero-Diels−Alder Reaction of Glyoxylate

  摘要：

  A highly enantioselective anti-diastereoselective hetero-Diets-Alder reaction between a glyoxylate and siloxy- or methoxydienes using a chiral phosphoric acid catalyst that possesses less bulky phenyl groups at the 3 and 3' positions of binaphthyl has been developed. The diastereoselectivities presented are disparate to those previously reported for hetero-Diets-Alder reactions catalyzed by a chiral Lewis acid.

  DOI：

  10.1021/ja904749x
• 作为产物：
  描述：

  (2S,6R)-6-Methyl-4-oxo-tetrahydro-pyran-2-carboxylic acid ethyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以67%的产率得到ethyl (2S,4S,6R)-4-hydroxy-6-methyloxane-2-carboxylate
  参考文献：
  名称：

  Chiral Phosphoric Acid-Governed Anti-Diastereoselective and Enantioselective Hetero-Diels−Alder Reaction of Glyoxylate

  摘要：

  A highly enantioselective anti-diastereoselective hetero-Diets-Alder reaction between a glyoxylate and siloxy- or methoxydienes using a chiral phosphoric acid catalyst that possesses less bulky phenyl groups at the 3 and 3' positions of binaphthyl has been developed. The diastereoselectivities presented are disparate to those previously reported for hetero-Diets-Alder reactions catalyzed by a chiral Lewis acid.

  DOI：

  10.1021/ja904749x