phenyl 2-O-benzyl-3,4-di-O-TIPS-1-thio-α-L-rhamnopyranoside sulfoxide | 1382228-89-8

• 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: phenyl 2-O-benzyl-3,4-di-O-TIPS-1-thio-α-L-rhamnopyranoside sulfoxide
• 英文别名: [(2S,3R,4S,5S,6S)-2-(benzenesulfinyl)-6-methyl-3-phenylmethoxy-5-tri(propan-2-yl)silyloxyoxan-4-yl]oxy-tri(propan-2-yl)silane
• CAS: 1382228-89-8
• 化学式: C₃₇H₆₂O₅SSi₂
• 分子量: 675.133
• InChiKey: NFZQDSQPCWEIPA-AAUPOADASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.25
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  73.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-benzyl-3,4-di-O-TIPS-1-thio-α-L-rhamnopyranoside sulfoxide 、 环己醇 在 三氟甲磺酸酐 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以27%的产率得到cyclohexyl 2-O-benzyl-3,4-di-O-TIPS-α-L-rhamnopyranoside
  参考文献：
  名称：

  Rhamnosylation: Diastereoselectivity of Conformationally Armed Donors

  摘要：

  The alpha/beta-selectivity of super-armed rhamnosyl donors have been investigated in glycosylation reactions. The solvent was found to have a minor influence, whereas temperature was crucial for the diastereoselectivity. At very low temperature, a modest beta-selectivity could be obtained, and increasing temperature gave excellent a-selectivity. The donors were highly reactive, and activation was observed at temperatures as low as -107 degrees C. Different promoter systems and leaving groups were investigated, and only activation with a heterogeneous catalyst increased the amount of the beta-anomer significantly. By introducing an electron-withdrawing nonparticipating group, benzyl sulfonyl, on 2-O, an increase in beta-product was observed.

  DOI：

  10.1021/jo300591k
• 作为产物：
  描述：

  苯基-alpha-O-苄基-1-硫代-alpha-L-吡喃鼠李糖苷 在 2,6-二甲基吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 phenyl 2-O-benzyl-3,4-di-O-TIPS-1-thio-α-L-rhamnopyranoside sulfoxide
  参考文献：
  名称：

  Rhamnosylation: Diastereoselectivity of Conformationally Armed Donors

  摘要：

  The alpha/beta-selectivity of super-armed rhamnosyl donors have been investigated in glycosylation reactions. The solvent was found to have a minor influence, whereas temperature was crucial for the diastereoselectivity. At very low temperature, a modest beta-selectivity could be obtained, and increasing temperature gave excellent a-selectivity. The donors were highly reactive, and activation was observed at temperatures as low as -107 degrees C. Different promoter systems and leaving groups were investigated, and only activation with a heterogeneous catalyst increased the amount of the beta-anomer significantly. By introducing an electron-withdrawing nonparticipating group, benzyl sulfonyl, on 2-O, an increase in beta-product was observed.

  DOI：

  10.1021/jo300591k

文献信息

• Rhamnosylation: Diastereoselectivity of Conformationally Armed Donors
  作者：Mads Heuckendorff、Christian Marcus Pedersen、Mikael Bols

  DOI：10.1021/jo300591k

  日期：2012.7.6

  The alpha/beta-selectivity of super-armed rhamnosyl donors have been investigated in glycosylation reactions. The solvent was found to have a minor influence, whereas temperature was crucial for the diastereoselectivity. At very low temperature, a modest beta-selectivity could be obtained, and increasing temperature gave excellent a-selectivity. The donors were highly reactive, and activation was observed at temperatures as low as -107 degrees C. Different promoter systems and leaving groups were investigated, and only activation with a heterogeneous catalyst increased the amount of the beta-anomer significantly. By introducing an electron-withdrawing nonparticipating group, benzyl sulfonyl, on 2-O, an increase in beta-product was observed.