(2R,3R,4R,6R)-N,N,2-trimethyl-4-prop-2-enoxy-6-[(4,4,5,5-tetramethyl-1,3,2-dioxaphospholan-2-yl)oxy]oxan-3-amine | 1187824-44-7

• 分子结构分类: 有机化合物 - 有机磷化合物 - 亚磷酸三烷基酯
• 英文名称: (2R,3R,4R,6R)-N,N,2-trimethyl-4-prop-2-enoxy-6-[(4,4,5,5-tetramethyl-1,3,2-dioxaphospholan-2-yl)oxy]oxan-3-amine
• CAS: 1187824-44-7
• 化学式: C₁₇H₃₂NO₅P
• 分子量: 361.419
• InChiKey: QGNRXPJORSQUMS-KBUPBQIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5S)-5-ethyl-4,5-dihydroxycyclohex-2-en-1-one 、 (2R,3R,4R,6R)-N,N,2-trimethyl-4-prop-2-enoxy-6-[(4,4,5,5-tetramethyl-1,3,2-dioxaphospholan-2-yl)oxy]oxan-3-amine 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以23%的产率得到
  参考文献：
  名称：

  Synthesis of the Fully Glycosylated Cyclohexenone Core of Lomaiviticin A

  摘要：

  We describe two four-step sequences for conversion of the inexpensive reagent ethyl sorbate to either O-allyl-N,N-dimethyl-D-pyrrolosamine or O-allyl-L-oleandrose, protected forms of the 2,6-dideoxy sugar residues found in the complex bacterial metabolite lomaiviticin A. We also report a gram-scale synthesis of the highly-oxygenated cyclohexenone ring of this metabolite, and show this may be coupled with the aforementioned donors to form the bis(glycoside) 6. The longest linear sequence to 6 is nine steps.

  DOI：

  10.1021/ol901710b
• 作为产物：
  描述：

  2-氯-4,4,5,5-四甲基-1,3,2-二氧磷杂环戊烷 、 O-allyl-N,N-dimethyl-D-pyrrolosamine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到(2R,3R,4R,6R)-N,N,2-trimethyl-4-prop-2-enoxy-6-[(4,4,5,5-tetramethyl-1,3,2-dioxaphospholan-2-yl)oxy]oxan-3-amine
  参考文献：
  名称：

  Synthesis of the Fully Glycosylated Cyclohexenone Core of Lomaiviticin A

  摘要：

  We describe two four-step sequences for conversion of the inexpensive reagent ethyl sorbate to either O-allyl-N,N-dimethyl-D-pyrrolosamine or O-allyl-L-oleandrose, protected forms of the 2,6-dideoxy sugar residues found in the complex bacterial metabolite lomaiviticin A. We also report a gram-scale synthesis of the highly-oxygenated cyclohexenone ring of this metabolite, and show this may be coupled with the aforementioned donors to form the bis(glycoside) 6. The longest linear sequence to 6 is nine steps.

  DOI：

  10.1021/ol901710b

文献信息

• Synthesis of the Fully Glycosylated Cyclohexenone Core of Lomaiviticin A
  作者：Shivajirao L. Gholap、Christina M. Woo、P. C. Ravikumar、Seth B. Herzon

  DOI：10.1021/ol901710b

  日期：2009.10.1

  We describe two four-step sequences for conversion of the inexpensive reagent ethyl sorbate to either O-allyl-N,N-dimethyl-D-pyrrolosamine or O-allyl-L-oleandrose, protected forms of the 2,6-dideoxy sugar residues found in the complex bacterial metabolite lomaiviticin A. We also report a gram-scale synthesis of the highly-oxygenated cyclohexenone ring of this metabolite, and show this may be coupled with the aforementioned donors to form the bis(glycoside) 6. The longest linear sequence to 6 is nine steps.