2-[Hex-5-enyl(dimethyl)silyl]ethanol | 192126-00-4

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: 2-[Hex-5-enyl(dimethyl)silyl]ethanol
• CAS: 192126-00-4
• 化学式: C₁₀H₂₂OSi
• 分子量: 186.37
• InChiKey: BQGNEBOLFFXVIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[Hex-5-enyl(dimethyl)silyl]ethanol 在 偶氮二异丁腈 、 间氯过氧苯甲酸 作用下， 以 乙酸乙酯 、 苯 为溶剂， 反应 93.0h， 生成 Ethyl 3-[6-[2-hydroxyethyl(dimethyl)silyl]hexylsulfonyl]propanoate
  参考文献：
  名称：

  A 2-silylethanol-based anomeric linker for carbohydrates; transformation into 1-O-acyl derivatives

  摘要：

  The novel linker 4 was synthesized in three steps front hex-5-enyldimethylchlorosilane and glycosylated with 2,3,4,6-tetra-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate to give the corresponding linker beta-glycoside 5 (77%). Treatment of 5 with acetic anhydride and BF3 . OEt2 gave 1-O-acetyl-2,3,4,6-tetra-O-benzoyl-beta-D-galactose (similar to 90%), devoid of the alpha-anomer. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00880-0
• 作为产物：
  描述：

  5-己烯基二甲基氯硅烷 、 溴乙酸乙酯 在 lithium aluminium tetrahydride 、 锌 作用下， 生成 2-[Hex-5-enyl(dimethyl)silyl]ethanol
  参考文献：
  名称：

  A 2-silylethanol-based anomeric linker for carbohydrates; transformation into 1-O-acyl derivatives

  摘要：

  The novel linker 4 was synthesized in three steps front hex-5-enyldimethylchlorosilane and glycosylated with 2,3,4,6-tetra-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate to give the corresponding linker beta-glycoside 5 (77%). Treatment of 5 with acetic anhydride and BF3 . OEt2 gave 1-O-acetyl-2,3,4,6-tetra-O-benzoyl-beta-D-galactose (similar to 90%), devoid of the alpha-anomer. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00880-0

文献信息

• A linker for solid phase carbohydrate synthesis, permitting the introduction of variable anomeric functionality in the release step
  作者：Dirk Weigelt、Göran Magnusson

  DOI：10.1016/s0040-4039(98)00312-8

  日期：1998.4

  The novel linker methyl 2-(4-methoxycarbonylbutyldimethylsily)ethanol (3) was synthesized in 58% overall yield over four steps, starting from 2-(hexenyldimethylsilyl)ethanol. Galactopyranosylation of 3 and coupling of the resulting linker galactoside to aminomethylated polystyrene resin gave a material that could be efficiently de-O-benzoylated as well as O-propionylated. Treatment of the resin with

  从2-（己烯基二甲基甲硅烷基）乙醇开始，通过四个步骤以58％的总产率合成了新型的接头甲基2-（4-甲氧基羰基丁基二甲基甲硅烷基）乙醇（3）。3的半乳糖吡喃糖基化和所得的连接基半乳糖苷与氨基甲基化的聚苯乙烯树脂的偶联产生了可以被有效地去O-苯甲酰化以及被O-丙酰化的材料。在BF 3 ·OEt 2存在下用乙酸酐或丙酸酐处理树脂，得到相应的1- O-丙酰基或-乙酰基吡喃半乳糖。