phenyl 2-O-benzylsulfonyl-4-O-TIPS-1-thio-β-L-rhamnopyranoside | 1382229-08-4

• 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-4-O-TIPS-1-thio-β-L-rhamnopyranoside
• 英文别名: phenyl 2-O-sulfonylbenzyl-4-O-TIPS-1-thio-β-L-rhamnopyranoside；[(2R,3R,4R,5R,6S)-4-hydroxy-6-methyl-2-phenylsulfanyl-5-tri(propan-2-yl)silyloxyoxan-3-yl] phenylmethanesulfonate
• CAS: 1382229-08-4
• 化学式: C₂₈H₄₂O₆S₂Si
• 分子量: 566.855
• InChiKey: FBBOGNSZNCZGKK-OVTMDPFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-benzylsulfonyl-4-O-TIPS-1-thio-β-L-rhamnopyranoside 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 [(2S,3R,4R,5S,6S)-4-[tert-butyl(dimethyl)silyl]oxy-2-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-6-methyl-5-tri(propan-2-yl)silyloxyoxan-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 6.0h， 生成 phenyl 2-O-benzylsulfonyl-4-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.