phenyl 2-O-benzylsulfonyl-3,4-di-O-TIPS-1-thio-β-L-rhamnopyranoside | 1382229-12-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-benzylsulfonyl-3,4-di-O-TIPS-1-thio-β-L-rhamnopyranoside
• 英文别名: phenyl 2-O-sulfonylbenzyl-3,4-di-O-TIPS-1-thio-β-L-rhamnopyranoside；[(2R,3R,4R,5S,6S)-6-methyl-2-phenylsulfanyl-4,5-bis[tri(propan-2-yl)silyloxy]oxan-3-yl] phenylmethanesulfonate
• CAS: 1382229-12-0
• 化学式: C₃₇H₆₂O₆S₂Si₂
• 分子量: 723.199
• InChiKey: SEWPAJYRFZHVTG-RCNBIBPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.56
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-benzylsulfonyl-3,4-di-O-TIPS-1-thio-β-L-rhamnopyranoside 、 环己醇 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以62%的产率得到[(3R,4R,5S,6S)-2-cyclohexyloxy-6-methyl-4,5-bis[tri(propan-2-yl)silyloxy]oxan-3-yl] phenylmethanesulfonate
  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：

  phenyl 2,3,4-tri-O-acetyl-1-thio-β-L-rhamnopyranoside 在 吡啶 、 2,6-二甲基吡啶 、 甲醇 、 三氟化硼乙醚 、 水 、 sodium methylate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 phenyl 2-O-benzylsulfonyl-3,4-di-O-TIPS-1-thio-β-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

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.