<1,1-dimethyl-3-<(triisopropylsilyl)oxy>propyl>dimethyl<(trimethylsilyl)ethynyl>silane | 221189-21-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: <1,1-dimethyl-3-<(triisopropylsilyl)oxy>propyl>dimethyl<(trimethylsilyl)ethynyl>silane
• CAS: 221189-21-5
• 化学式: C₂₁H₄₆OSi₃
• 分子量: 398.852
• InChiKey: FBUSNJHMJAANSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.48
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  <1,1-dimethyl-3-<(triisopropylsilyl)oxy>propyl>dimethyl<(trimethylsilyl)ethynyl>silane 在 盐酸 、 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 正丁基锂 、 三氯化铝 、 P(fur)3 、 三甲基铝 、 sodium methylate 、 silver trifluoroacetate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二甲基亚砜 、 丙酮 为溶剂， 反应 40.5h， 生成 5,9-anhydro-1,2,3,4,8-pentadeoxy-8-C-<<(3-hydroxy-1,1-dimethylpropyl)dimethylsilyl>ethynyl>-6-O-(triisopropylsilyl)-D-glycero-D-gulo-deca-1,3-diynitol-1-yl-(1->6-C)-3,7-anhydro-1,2,6-trideoxy-4-O-(triisopropylsilyl)-1-C-(trimethylsilyl)-D-glycero-D-g...
  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：

  三异丙基硅基三氟甲磺酸酯 、 3-silyl>-3-methylbutan-1-ol 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到<1,1-dimethyl-3-<(triisopropylsilyl)oxy>propyl>dimethyl<(trimethylsilyl)ethynyl>silane
  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

文献信息

• Oligosaccharide Analogues of Polysaccharides, Part 16, Cross-Coupling of Partially Protected Dialkynyl Monosaccharides
  作者：Tanja Verena Bohner、Renaud Beaudegnies、Andrea Vasella

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

  日期：1999.2.10

  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.