1,2-O-isopropylidene-5-O-methoxymethyl-6-(3-trimethylsilyl-prop-2-ynyl)-α-D-glucofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-5-O-methoxymethyl-6-(3-trimethylsilyl-prop-2-ynyl)-α-D-glucofuranose
• 英文别名: (3aR,5S,6S,6aR)-5-[(1R)-2-hydroxy-1-(methoxymethoxy)-5-trimethylsilylpent-4-ynyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• 化学式: C₁₇H₃₀O₇Si
• 分子量: 374.507
• InChiKey: LZXNTUHKYYJAKK-AHWBYSNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-5-O-methoxymethyl-6-(3-trimethylsilyl-prop-2-ynyl)-α-D-glucofuranose 在 potassium carbonate 、 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 甲醇 、 丙酮 、 乙腈 、 叔丁醇 为溶剂， 反应 11.0h， 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
• 作为产物：
  描述：

  1-(三甲基硅基)丙炔 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 1.0h， 生成 1,2-O-isopropylidene-5-O-methoxymethyl-6-(3-trimethylsilyl-prop-2-ynyl)-α-D-glucofuranose
  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

文献信息

• Formation of Five- and Six-Membered Carbocycles with Nitrogenated Tetrasubstituted Carbons by Radical Addition-Carbocyclization of Alkynyl Ketoxime Ethers
  作者：Marta Fernández-González、Ricardo Alonso

  DOI：10.1021/jo060883y

  日期：2006.9.1

  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.