3,7-anhydro-1,2,6-trideoxy-6-C-<(4-nitrophenyl)ethynyl>-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol | 221189-62-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,7-anhydro-1,2,6-trideoxy-6-C-<(4-nitrophenyl)ethynyl>-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol
• CAS: 221189-62-4
• 化学式: C₂₅H₃₅NO₆Si
• 分子量: 473.642
• InChiKey: VKBYUFNCGYBVIZ-KJWQXZETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  102.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,7-anhydro-1,2,6-trideoxy-6-C-<(4-nitrophenyl)ethynyl>-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol 在 N-溴代丁二酰亚胺(NBS) 、 silver trifluoroacetate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以97%的产率得到3,7-anhydro-1-C-bromo-1,2,6-trideoxy-6-C-<(4-nitrophenyl)ethynyl>-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol
  参考文献：
  名称：

  Oligosaccharide Analogues of Polysaccharides, Part 16, Cross-Coupling of Partially Protected Dialkynyl Monosaccharides

  摘要：

  The dependency of the cross-coupling of orthogonally C-protected dialkynyl monosaccharides on the nature of the coupling partners has been studied, The required dialkyne 5 was synthesized from levoglucosan in six steps and 39% overall yield and transformed into 7 10, 12, 13, and 14 by orthogonal C-deprotection and bromination (Scheme 1). Optimization of the conditions of their cross-coupling to 16 showed that yields were higher for the coupling of the propargylic bromoalkyne 10 than for the homopropargylic bromoalkyne 14 (Scheme 2). Deprotection of 16 gave the nano-crystalline dimer 20. To obtain more highly crystalline products, the monomers 7 and 13 were coupled with 1-iodo-4-nitrobenzene to the arylated monomers 21 and 24 (Scheme 3). The 4-NO2C6H4, substituent lowered the yield of the dimerizations to the mono- and diarylated dimers 26-28 (Scheme 4) but had no effect on crystallinity.

  DOI：

  10.1002/(sici)1522-2675(19990210)82:2<143::aid-hlca143>3.0.co;2-0
• 作为产物：
  描述：

  3,7-anhydro-1,1,2,2-tetradehydro-1,2,6-trideoxy-6-C-ethynyl-4-O-(triisopropylsilyl)-1-C-(trimethylsilyl)-D-glycero-D-gulo-octitol 在 copper(l) iodide 、 四(三苯基膦)钯 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 23.0h， 生成 3,7-anhydro-1,2,6-trideoxy-6-C-<(4-nitrophenyl)ethynyl>-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol
  参考文献：
  名称：

  Oligosaccharide Analogues of Polysaccharides, Part 16, Cross-Coupling of Partially Protected Dialkynyl Monosaccharides

  摘要：

  The dependency of the cross-coupling of orthogonally C-protected dialkynyl monosaccharides on the nature of the coupling partners has been studied, The required dialkyne 5 was synthesized from levoglucosan in six steps and 39% overall yield and transformed into 7 10, 12, 13, and 14 by orthogonal C-deprotection and bromination (Scheme 1). Optimization of the conditions of their cross-coupling to 16 showed that yields were higher for the coupling of the propargylic bromoalkyne 10 than for the homopropargylic bromoalkyne 14 (Scheme 2). Deprotection of 16 gave the nano-crystalline dimer 20. To obtain more highly crystalline products, the monomers 7 and 13 were coupled with 1-iodo-4-nitrobenzene to the arylated monomers 21 and 24 (Scheme 3). The 4-NO2C6H4, substituent lowered the yield of the dimerizations to the mono- and diarylated dimers 26-28 (Scheme 4) but had no effect on crystallinity.

  DOI：

  10.1002/(sici)1522-2675(19990210)82:2<143::aid-hlca143>3.0.co;2-0