1-[4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-hydroxybenzene | 651035-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-[4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-hydroxybenzene
• 英文别名: 4-[(2R,3S,6R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,6-dihydro-2H-pyran-6-yl]phenol
• CAS: 651035-36-8
• 化学式: C₂₄H₄₂O₄Si₂
• 分子量: 450.766
• InChiKey: UGOVHBOJPADZLH-BHIFYINESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-[4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-hydroxybenzene 在 [Rh(COD)(1,4-bis(diphenylphosphino)butane)]ClO₄ 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 29.0h， 生成 1-(2,3-dideoxy-β-D-erythro-hexanopyranosyl)-4-hydroxybenzene
  参考文献：
  名称：

  Enantiopure Trioxadecalin Derived Liquid Crystals: Influence of the Nature of the Phenyl Substituent on the Mesogenic Properties

  摘要：

  Reaction of pseudo-glucal 1 with Grignard reagents derived from 1-bromo-4(trimethylsilyloxy)benzene, 1-bromo-4-methoxybenzene, 1-bromo-4-methoxymethoxybenzene, 1-bromo-4-dimethylaminobenzene, in the presence of a catalytic amount of NiCl2(dppe), gives the corresponding unsaturated beta-C-aryl glycosides 2. Desilylation and hydrogenation of 2 leads to beta-C-aryl glycosides 4, which can be used as chiral precursor compounds in the synthesis of chiral liquid crystals. Combination of 4 with arylaldehydes leads to compounds 5-7, whereas reaction with p-alkoxysubstituted phenylboronic acids gives the trioxaboradecalins 8-11. The mesogenic properties of these compounds are strongly influenced by the nature of the substituent on the phenyl ring in the molecule.

  DOI：

  10.1081/car-120026468
• 作为产物：
  描述：

  对(三甲基硅氧基)溴苯 、 p-tert-butylphenyl 4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 magnesium 、 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48%的产率得到1-[4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-hydroxybenzene
  参考文献：
  名称：

  Enantiopure Trioxadecalin Derived Liquid Crystals: Influence of the Nature of the Phenyl Substituent on the Mesogenic Properties

  摘要：

  Reaction of pseudo-glucal 1 with Grignard reagents derived from 1-bromo-4(trimethylsilyloxy)benzene, 1-bromo-4-methoxybenzene, 1-bromo-4-methoxymethoxybenzene, 1-bromo-4-dimethylaminobenzene, in the presence of a catalytic amount of NiCl2(dppe), gives the corresponding unsaturated beta-C-aryl glycosides 2. Desilylation and hydrogenation of 2 leads to beta-C-aryl glycosides 4, which can be used as chiral precursor compounds in the synthesis of chiral liquid crystals. Combination of 4 with arylaldehydes leads to compounds 5-7, whereas reaction with p-alkoxysubstituted phenylboronic acids gives the trioxaboradecalins 8-11. The mesogenic properties of these compounds are strongly influenced by the nature of the substituent on the phenyl ring in the molecule.

  DOI：

  10.1081/car-120026468