3,7-anhydro-1,2,6-trideoxy-6-C-<propyl>silyl>ethynyl>-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol | 221189-27-1

• 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-<propyl>silyl>ethynyl>-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol
• 英文别名: (2S,3R,4S,5S,6S)-5-[2-[dimethyl-[2-methyl-4-tri(propan-2-yl)silyloxybutan-2-yl]silyl]ethynyl]-2-ethynyl-6-(hydroxymethyl)-3-tri(propan-2-yl)silyloxyoxan-4-ol
• CAS: 221189-27-1
• 化学式: C₃₅H₆₈O₅Si₃
• 分子量: 653.178
• InChiKey: MRHUABUKBOFWND-BBZHULIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.53
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,7-anhydro-1,2,6-trideoxy-6-C-<propyl>silyl>ethynyl>-4-O-(triisopropylsilyl)-D-glycero-D-gulo-oct-1-ynitol 在 盐酸 、 tris-(dibenzylideneacetone)dipalladium(0) 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 P(fur)3 、 silver trifluoroacetate 、 三乙胺 作用下， 以 乙醇 、 二甲基亚砜 、 丙酮 为溶剂， 反应 14.0h， 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：

  1,6-anhydro-4-deoxy-4-C-propyl>silyl>ethynyl>-2-O-(triisopropylsilyl)-β-D-glucopyranose 在 正丁基锂 、 三氯化铝 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 21.5h， 生成 3,7-anhydro-1,2,6-trideoxy-6-C-<propyl>silyl>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