(1S,4S,5R,6S)-4-methyl-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-5-yl acetate | 941703-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1S,4S,5R,6S)-4-methyl-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-5-yl acetate
• CAS: 941703-48-6
• 化学式: C₈H₁₀O₅
• 分子量: 186.164
• InChiKey: GRLINBZRKMPDOB-CDGOZMSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.37
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  65.13
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S,4S,5R,6S)-4-methyl-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-5-yl acetate 在 吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 六氟磷酸银 、 二苯基二硒醚 、 三氟化硼乙醚 、 二异丁基氢化铝 、 potassium carbonate 、 异丙醇 、 2,4,6-三叔丁基嘧啶 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 7.0h， 生成 7-(3-azido-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)daunorubicinone
  参考文献：
  名称：

  A divergent approach to 3-azido-2,3,6-trideoxy-l-hexoses from rhamnal

  摘要：

  An alternative strategy has been developed for producing 3-azido-2,3,6-trideoxy-L-hexoses, protected forms of daunosamine, ristosamine, acosamine, and epi-daunosamine. This method involved BF3-OEt2-induced peroxidation of rhamnal to construct key intermediate alpha,beta-unsaturated lactone as the common precursor. After further derivatization, four 3-azido hexoses were successfully synthesized. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.062
• 作为产物：
  描述：

  (2S,3S)-5-acetoxy-6-methyl-5,6-dihydropyran-2-one 在 过氧化氢苯甲酰 作用下， 以 苯 为溶剂， 反应 30.0h， 生成 (1S,4S,5R,6S)-4-methyl-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-5-yl acetate
  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