(1S,4S,5R,6S)-5-hydroxy-4-methyl-3,7-dioxabicyclo[4.1.0]heptan-2-one | 952426-03-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: (1S,4S,5R,6S)-5-hydroxy-4-methyl-3,7-dioxabicyclo[4.1.0]heptan-2-one
• CAS: 952426-03-8
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: QRCXZIJLWABTSX-QTBDOELSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.94
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  59.06
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,4S,5R,6S)-5-hydroxy-4-methyl-3,7-dioxabicyclo[4.1.0]heptan-2-one 在 sodium tetrahydroborate 、 二苯基二硒醚 、 溶剂黄146 作用下， 以 异丙醇 为溶剂， 反应 1.0h， 生成 (4R,5S,6S)-4,5-dihydroxy-6-methyltetrahydropyran-2-one
  参考文献：
  名称：

  A divergent strategy for constructing a sugar library containing 2,6-dideoxy sugars and uncommon sugars with 4-substitution

  摘要：

  A practical strategy has been developed for delivering 2,6-dideoxy sugars and uncommon sugars with 4-substitution. This strategy employed Ferrier rearrangement reaction and BF3 center dot OEt2-induced peroxidation to construct key intermediates 2,3-unsaturated glycosides and alpha,beta-unsaturated lactones from peracetyl rhamnal. After further derivatization, four uncommon sugars with 4-substitution and eight uncommon sugar units with 3,4-disubstitution were successfully synthesized. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.019
• 作为产物：
  描述：

  (1S,4S,5R,6S)-4-methyl-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-5-yl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (1S,4S,5R,6S)-5-hydroxy-4-methyl-3,7-dioxabicyclo[4.1.0]heptan-2-one
  参考文献：
  名称：

  A divergent strategy for constructing a sugar library containing 2,6-dideoxy sugars and uncommon sugars with 4-substitution

  摘要：

  A practical strategy has been developed for delivering 2,6-dideoxy sugars and uncommon sugars with 4-substitution. This strategy employed Ferrier rearrangement reaction and BF3 center dot OEt2-induced peroxidation to construct key intermediates 2,3-unsaturated glycosides and alpha,beta-unsaturated lactones from peracetyl rhamnal. After further derivatization, four uncommon sugars with 4-substitution and eight uncommon sugar units with 3,4-disubstitution were successfully synthesized. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.019