(3S,5S)-5-acetoxy-2-benzyl-3-(1,2-O-isopropylidene-3-O-benzyl-4-O-tert-butyldiphenylsilyl-D-xylos-1-yl)isoxazolidine | 1021461-65-3

• 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: (3S,5S)-5-acetoxy-2-benzyl-3-(1,2-O-isopropylidene-3-O-benzyl-4-O-tert-butyldiphenylsilyl-D-xylos-1-yl)isoxazolidine
• 英文别名: [(3S,5S)-2-benzyl-3-[(4S,5R)-5-[(1R)-2-[tert-butyl(diphenyl)silyl]oxy-1-phenylmethoxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2-oxazolidin-5-yl] acetate
• CAS: 1021461-65-3
• 化学式: C₄₂H₅₁NO₇Si
• 分子量: 709.955
• InChiKey: WPILLLDCBBRBSJ-DRTMTWGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.76
• 重原子数：
  51
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  75.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-2-乙酰鸟嘌呤 、 (3S,5S)-5-acetoxy-2-benzyl-3-(1,2-O-isopropylidene-3-O-benzyl-4-O-tert-butyldiphenylsilyl-D-xylos-1-yl)isoxazolidine 在 牛血清白蛋白 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 以15%的产率得到1-[(3S,5R)-2-benzyl-3-(1,2-O-isopropylidene-3-O-benzyl-4-O-tert-butyldiphenylsilyl-D-xylos-1-yl)isoxazolidin-5-yl]-2-acetylguanine
  参考文献：
  名称：

  Diastereoselective synthesis of d-xylo-isoxazolidinyl nucleosides

  摘要：

  The condensation of the acetoxyisoxazolidines with silylated uracil, thymine, cytosine, N-acetylcytosine, and guanine proceeded in good yields and with moderate to good stereoselectivity to give isoxazolidinyl beta- and alpha-nucleosides. The stereoselectivity of the addition is dependent on the structure of the substituent at C-3 originating from the starting chiral nitrone. The Vorbruggen nucleosidation of isoxazolidine 8 at 70 degrees C afforded beta-anomers as the exclusive nucleosides together with the isoxazoline 11. It was found that the nucleosidation proceeded also in methylene chloride at room temperature. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.133
• 作为产物：
  描述：

  乙酸乙烯酯 、 (Z)-N-(1-deoxy-2,3-O-isopropylidene-4-O-benzyl-5-O-tert-butyldiphenylsilyl-D-xylos-1-ylidene)benzylamine-N-oxide 反应 24.0h， 以74%的产率得到(3S,5S)-5-acetoxy-2-benzyl-3-(1,2-O-isopropylidene-3-O-benzyl-4-O-tert-butyldiphenylsilyl-D-xylos-1-yl)isoxazolidine
  参考文献：
  名称：

  Diastereoselective synthesis of d-xylo-isoxazolidinyl nucleosides

  摘要：

  The condensation of the acetoxyisoxazolidines with silylated uracil, thymine, cytosine, N-acetylcytosine, and guanine proceeded in good yields and with moderate to good stereoselectivity to give isoxazolidinyl beta- and alpha-nucleosides. The stereoselectivity of the addition is dependent on the structure of the substituent at C-3 originating from the starting chiral nitrone. The Vorbruggen nucleosidation of isoxazolidine 8 at 70 degrees C afforded beta-anomers as the exclusive nucleosides together with the isoxazoline 11. It was found that the nucleosidation proceeded also in methylene chloride at room temperature. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.133