(3S,4'S)-diethyl [2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-3,6-dihydro-2H-1,2-oxazin-4-yl]phosphate | 1122571-80-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4'S)-diethyl [2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-3,6-dihydro-2H-1,2-oxazin-4-yl]phosphate
• 英文别名: [(3S)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,6-dihydrooxazin-4-yl] diethyl phosphate
• CAS: 1122571-80-5
• 化学式: C₂₀H₃₀NO₇P
• 分子量: 427.434
• InChiKey: ROLXOSUCJDXYPL-RTBURBONSA-N

物化性质

• 沸点：
  489.3±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  75.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S,4'S)-diethyl [2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-3,6-dihydro-2H-1,2-oxazin-4-yl]phosphate 在 indium(III) chloride 、 水 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以97%的产率得到[(3S)-2-benzyl-3-[(1S)-1,2-dihydroxyethyl]-3,6-dihydrooxazin-4-yl] diethyl phosphate
  参考文献：
  名称：

  Indium Trichloride Mediated Cleavage of Acetonides in the Presence of Acid-Labile Functional Groups - Enhancing the Synthetic Utility of 1,3-Dioxolanyl-Substituted 1,2-Oxazines

  摘要：

  三氯化铟在乙腈-水混合物中能化学选择性地裂解各种 1,3- 二氧戊环取代的 1,2- 氧嗪的异亚丙基乙醛以及碳水化合物衍生物。在易受酸诱导环化作用影响的底物中，可以实现丙酮的脱保护。最重要的是，烯醇醚分子不会受到侵蚀，而且还能承受糖苷键或对酸敏感的保护基团（如叔丁基二甲基硅基、2-（三甲基硅基）乙基或叔丁氧基羰基）的存在。

  DOI：

  10.1055/s-0028-1083628
• 作为产物：
  描述：

  (3S,4′S)-2-benzyl-5-bromo-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-3,4,5,6-tetrahydro-2H-1,2-oxazin-4-one 在 亚磷酸三乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以90%的产率得到(3S,4'S)-diethyl [2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-3,6-dihydro-2H-1,2-oxazin-4-yl]phosphate
  参考文献：
  名称：

  Convenient Syntheses of Enantiopure 1,2-Oxazin-4-yl Nonaflates and Phosphates and Their Palladium-Catalyzed Cross-Couplings

  摘要：

  Efficient methods to prepare enantiopure 1,2-oxazin-4-yl nonaflates and phosphates were elaborated. The corresponding 1,2-oxazin-4-ones were transformed into their enolates and then quenched with nonafluorobutanesulfonyl fluoride or diphenyl chlorophosphate to provide the title compounds. Alternatively, the corresponding -bromo ketones were subjected to Perkow reactions efficiently leading to the respective enol phosphates. A variety of palladium-catalyzed cross-couplings such as Kumada-Corriu, Sonogashira, Heck reactions or borylation reactions were studied, which delivered the expected new 4-substituted 1,2-oxazine derivatives generally in satisfactory yields. A few typical subsequent transformations were studied including a copper-catalyzed [3+2] cycloaddition with a galactose-derived azide. They demonstrate the synthetic potential of the newly prepared enantiopure 4-substituted 1,2-oxazines.

  DOI：

  10.1055/s-0033-1339509