4-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]biphenyl | 368452-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]biphenyl
• 英文别名: tert-butyl-[[(2R,3S,6R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(4-phenylphenyl)-3,6-dihydro-2H-pyran-3-yl]oxy]-dimethylsilane
• CAS: 368452-20-4
• 化学式: C₃₀H₄₆O₃Si₂
• 分子量: 510.864
• InChiKey: SUHFSPMNNSRHJY-OZNIXHKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.76
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]biphenyl 在 [Rh(COD)(1,4-bis(diphenylphosphino)butane)]ClO₄ 四丁基氯化铵 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 生成 (1S,3R,6R,8R)-8-biphenyl-3-(4'-octyloxyphenyl)-2,4,7-trioxabicyclo[4.4.0]decane
  参考文献：
  名称：

  ENANTIOPURE TRIOXADECALIN DERIVED LIQUID CRYSTALS: INFLUENCE OF PHENYL SUBSTITUTION ON THE MESOGENIC PROPERTIES

  摘要：

  Nickel(0)-catalyzed reaction of pseudo-glucal 1 with Grignard reagents derived from bromobenzene and 1-bromo-4-phenylbenzene gives the corresponding beta -C-aryl glycosides 2. Desilylation and hydrogenation of 2 leads to saturated beta -C-aryl glycosides 4, which can be used as chiral intermediates in the synthesis of chiral liquid crystals. The combination with p-alkoxy-substituted benzaldehyde leads to compounds 5-6. Alternatively, reaction with p-alkoxy-substituted phenylboronic acids gives the bora analogues 7-9. The mesogenic properties of these compounds are strongly influenced by the presence of an additional phenyl ring in the molecule.

  DOI：

  10.1081/car-100104867
• 作为产物：
  描述：

  2-BIPHENYLMAGNESIUM BROMIDE 、 p-tert-butylphenyl 4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 1,2-双(二苯基膦)乙烷氯化镍 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以71%的产率得到4-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]biphenyl
  参考文献：
  名称：

  ENANTIOPURE TRIOXADECALIN DERIVED LIQUID CRYSTALS: INFLUENCE OF PHENYL SUBSTITUTION ON THE MESOGENIC PROPERTIES

  摘要：

  Nickel(0)-catalyzed reaction of pseudo-glucal 1 with Grignard reagents derived from bromobenzene and 1-bromo-4-phenylbenzene gives the corresponding beta -C-aryl glycosides 2. Desilylation and hydrogenation of 2 leads to saturated beta -C-aryl glycosides 4, which can be used as chiral intermediates in the synthesis of chiral liquid crystals. The combination with p-alkoxy-substituted benzaldehyde leads to compounds 5-6. Alternatively, reaction with p-alkoxy-substituted phenylboronic acids gives the bora analogues 7-9. The mesogenic properties of these compounds are strongly influenced by the presence of an additional phenyl ring in the molecule.

  DOI：

  10.1081/car-100104867