(6R)-3-benzyloxyimino-1,2:5,6-di-O-isopropylidene-6-(prop-2-ynyl)-α-D-ribohexofuranose | 911407-82-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (6R)-3-benzyloxyimino-1,2:5,6-di-O-isopropylidene-6-(prop-2-ynyl)-α-D-ribohexofuranose
• CAS: 911407-82-4
• 化学式: C₂₂H₂₇NO₆
• 分子量: 401.459
• InChiKey: FXHQNHLQWOBEMF-XIKSMUEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  67.74
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (6R)-3-benzyloxyimino-1,2:5,6-di-O-isopropylidene-6-(prop-2-ynyl)-α-D-ribohexofuranose 、 苯硫酚 以 苯 为溶剂， 反应 5.5h， 生成 、 、 、 (1S,2R,6R,8E,9R,10R,14R)-4,4,12,12-tetramethyl-N-phenylmethoxy-8-(phenylsulfanylmethylidene)-3,5,11,13,15-pentaoxatetracyclo[7.6.0.02,6.010,14]pentadecan-9-amine
  参考文献：
  名称：

  Formation of Five- and Six-Membered Carbocycles with Nitrogenated Tetrasubstituted Carbons by Radical Addition-Carbocyclization of Alkynyl Ketoxime Ethers

  摘要：

  C3-Ketoxime ethers bearing alkynes with terminal delta-yne or internal gamma-yne functions were prepared in five or six steps and similar to 20% overall yield from commercial glucofuranose derivatives. Their thiyl-, stannyl-, or carbon radical-promoted addition-carbocyclization gave five- or six-membered carbocycles nitrogenated at one of the bridgehead positions. For internal gamma-yne ethers the tandem process was strongly dependent on both the alkyne substituent and the radical-promoting species and could be directed toward either the five- or the six-membered carbocycle. These results are presented and discussed in the context of studies working toward (-)-tetrodotoxin.

  DOI：

  10.1021/jo060883y
• 作为产物：
  描述：

  D-glucurono-3,6-lactone acetonide 在 sodium tetrahydroborate 、 正丁基锂 、 potassium carbonate 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 丙酮 、 乙腈 、 叔丁醇 为溶剂， 反应 12.0h， 生成 (6R)-3-benzyloxyimino-1,2:5,6-di-O-isopropylidene-6-(prop-2-ynyl)-α-D-ribohexofuranose
  参考文献：
  名称：

  Formation of Five- and Six-Membered Carbocycles with Nitrogenated Tetrasubstituted Carbons by Radical Addition-Carbocyclization of Alkynyl Ketoxime Ethers

  摘要：

  C3-Ketoxime ethers bearing alkynes with terminal delta-yne or internal gamma-yne functions were prepared in five or six steps and similar to 20% overall yield from commercial glucofuranose derivatives. Their thiyl-, stannyl-, or carbon radical-promoted addition-carbocyclization gave five- or six-membered carbocycles nitrogenated at one of the bridgehead positions. For internal gamma-yne ethers the tandem process was strongly dependent on both the alkyne substituent and the radical-promoting species and could be directed toward either the five- or the six-membered carbocycle. These results are presented and discussed in the context of studies working toward (-)-tetrodotoxin.

  DOI：

  10.1021/jo060883y