5,9-anhydro-1,2,3,4,8-pentadeoxy-8-C-<(4-nitrophenyl)ethynyl>-6-O-(triisopropylsilyl)-D-glycero-D-gulo-deca-1,3-diynitol-1-yl-(1->6-C)-3,7-anhydro-1,2,6-trideoxy-1-C-(4-nitrophenyl)-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol | 221189-79-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,9-anhydro-1,2,3,4,8-pentadeoxy-8-C-<(4-nitrophenyl)ethynyl>-6-O-(triisopropylsilyl)-D-glycero-D-gulo-deca-1,3-diynitol-1-yl-(1->6-C)-3,7-anhydro-1,2,6-trideoxy-1-C-(4-nitrophenyl)-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol
• 英文别名: (2S,3S,4S,5R,6S)-3-[4-[(2S,3R,4S,5S,6S)-4-hydroxy-6-(hydroxymethyl)-5-[2-(4-nitrophenyl)ethynyl]-3-tri(propan-2-yl)silyloxyoxan-2-yl]buta-1,3-diynyl]-2-(hydroxymethyl)-6-[2-(4-nitrophenyl)ethynyl]-5-tri(propan-2-yl)silyloxyoxan-4-ol
• CAS: 221189-79-3
• 化学式: C₅₀H₆₈N₂O₁₂Si₂
• 分子量: 945.267
• InChiKey: VPFITFVAIVXZNW-GXUQQTCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  66
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  210
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5,9-anhydro-1,2,3,4,8-pentadeoxy-8-C-<(4-nitrophenyl)ethynyl>-6-O-(triisopropylsilyl)-D-glycero-D-gulo-deca-1,3-diynitol-1-yl-(1->6-C)-3,7-anhydro-1,2,6-trideoxy-1-C-(4-nitrophenyl)-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 45.0h， 以97%的产率得到5,9-anhdyro-1,2,3,4,8-pentadeoxy-8-C-<(4-nitrophenyl)ethynyl>-D-glycero-D-gulo-deca-1,3-diynitol-1-yl-(1->6-C)-3,7-anhdyro-1,2,6-trideoxy-1-C-(4-nitrophenyl)-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-1,2,6-trideoxy-6-C-<<(3-hydroxy-1,1-dimethylpropyl)dimethylsilyl>ethynyl>-4-O-(triisopropylsilyl)-1-C-(trimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol 在 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 四(三苯基膦)钯 、 杀鼠酮 、 silver trifluoroacetate 、 二甲基亚砜 、 三乙胺 、 lithium iodide 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 63.0h， 生成 5,9-anhydro-1,2,3,4,8-pentadeoxy-8-C-<(4-nitrophenyl)ethynyl>-6-O-(triisopropylsilyl)-D-glycero-D-gulo-deca-1,3-diynitol-1-yl-(1->6-C)-3,7-anhydro-1,2,6-trideoxy-1-C-(4-nitrophenyl)-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