[(2S,4R,5S)-5-Benzyloxy-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yl]-methanol | 228122-10-9

• 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: [(2S,4R,5S)-5-Benzyloxy-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yl]-methanol
• 英文别名: [(2S,4R,5S)-4-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-2-(4-methoxyphenyl)-5-phenylmethoxy-1,3-dioxan-5-yl]methanol
• CAS: 228122-10-9
• 化学式: C₂₇H₄₀O₆Si
• 分子量: 488.697
• InChiKey: XSGZPJOZPQLDAH-OBDYRVMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S,4R,5S)-5-Benzyloxy-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yl]-methanol 在 N-甲基吲哚酮 、 四丙基高钌酸铵 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(2S,4R,5S)-4-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-2-(4-methoxyphenyl)-5-phenylmethoxy-1,3-dioxane-5-carbaldehyde
  参考文献：
  名称：

  Synthesis of stereodefined Z-vinyl iodides from carbohydrates as a prelude to C/D ring assembly in taxanes

  摘要：

  D-Mannitol has been transformed into 10 and 14, while D-glucose has served as precursor to 20. In the latter example, key steps include stereocontrolled vinylation, oxidative fragmentation of the tetrahydrofuran-2,3-diol, oxetane ring closure, and highly stereoselective iodoolefination. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00546-8
• 作为产物：
  描述：

  (2S,3R)-2-(benzyloxy)-3-<(p-methoxybenzyl)oxy>-2-<<(p-methoxybenzyl)oxy>methyl>-4-pentenal 在 咪唑 、 4-二甲氨基吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 生成 [(2S,4R,5S)-5-Benzyloxy-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yl]-methanol
  参考文献：
  名称：

  Synthesis of stereodefined Z-vinyl iodides from carbohydrates as a prelude to C/D ring assembly in taxanes

  摘要：

  D-Mannitol has been transformed into 10 and 14, while D-glucose has served as precursor to 20. In the latter example, key steps include stereocontrolled vinylation, oxidative fragmentation of the tetrahydrofuran-2,3-diol, oxetane ring closure, and highly stereoselective iodoolefination. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00546-8

文献信息

• Synthesis of stereodefined Z-vinyl iodides from carbohydrates as a prelude to C/D ring assembly in taxanes
  作者：Leo A. Paquette、Tzenge-Lien Shih、Qingbei Zeng、John E. Hofferberth

  DOI：10.1016/s0040-4039(99)00546-8

  日期：1999.4

  D-Mannitol has been transformed into 10 and 14, while D-glucose has served as precursor to 20. In the latter example, key steps include stereocontrolled vinylation, oxidative fragmentation of the tetrahydrofuran-2,3-diol, oxetane ring closure, and highly stereoselective iodoolefination. (C) 1999 Elsevier Science Ltd. All rights reserved.