[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[2-[6-(3-ethoxy-3-oxopropyl)sulfonylhexyl-dimethylsilyl]ethoxy]oxan-2-yl]methyl benzoate | 192126-03-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[2-[6-(3-ethoxy-3-oxopropyl)sulfonylhexyl-dimethylsilyl]ethoxy]oxan-2-yl]methyl benzoate
• CAS: 192126-03-7
• 化学式: C₄₉H₅₈O₁₄SSi
• 分子量: 931.143
• InChiKey: YWCREPCEGDTTIX-KXXCFAEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  65
• 可旋转键数：
  29
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  193
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 [(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[2-[6-(3-ethoxy-3-oxopropyl)sulfonylhexyl-dimethylsilyl]ethoxy]oxan-2-yl]methyl benzoate 在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以90%的产率得到1-O-acetyl-2,3,4,6-tetra-O-benzoyl-β-D-galactopyranose
  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 、 三氟甲磺酸三甲基硅酯 、 间氯过氧苯甲酸 作用下， 以 正庚烷 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 93.33h， 生成 [(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

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.