Ethyl 3-[6-[2-hydroxyethyl(dimethyl)silyl]hexylsulfonyl]propanoate | 192126-02-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: Ethyl 3-[6-[2-hydroxyethyl(dimethyl)silyl]hexylsulfonyl]propanoate
• CAS: 192126-02-6
• 化学式: C₁₅H₃₂O₅SSi
• 分子量: 352.568
• InChiKey: XACCCWZHNRCHMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-1-O-trichloroacetimidoyl-α-D-galactopyranose 、 Ethyl 3-[6-[2-hydroxyethyl(dimethyl)silyl]hexylsulfonyl]propanoate 在 三氟甲磺酸三甲基硅酯 作用下， 以 正庚烷 、 二氯甲烷 为溶剂， 反应 0.33h， 以77%的产率得到[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[2-[6-(3-ethoxy-3-oxopropyl)sulfonylhexyl-dimethylsilyl]ethoxy]oxan-2-yl]methyl benzoate
  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：

  3-巯基丙酸乙酯 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

文献信息

• A 2-silylethanol-based anomeric linker for carbohydrates; transformation into 1-O-acyl derivatives
  作者：Andreas Wållberg、Dirk Weigelt、Niklas Falk、Göran Magnusson

  DOI：10.1016/s0040-4039(97)00880-0

  日期：1997.6

  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.