(2R,3S,4S,5S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-5-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4,5-dihydroxy-pentanal | 151265-97-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-5-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4,5-dihydroxy-pentanal
• CAS: 151265-97-3
• 化学式: C₂₉H₆₂O₈Si₃
• 分子量: 623.063
• InChiKey: KUEVAENYYMEWPZ-WUYMVFMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  40.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  103.68
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-5-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4,5-dihydroxy-pentanal 在 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 生成 (2R,3S,4S,5R,6R,7S)-2,3,5,6,7,8-Hexahydroxyoctanoic acid γ-lactone
  参考文献：
  名称：

  Stereoselective synthesis of long-chain polyols by sequential homologation of enals with nonracemic .gamma.-silyloxy allylic stannanes and directed hydroxylation

  摘要：

  The nonracemic gamma-silyloxy allylic stannanes (S)-8 and (R)-8 add to the (R,R)-tartrate derived enals 7 and 24 to afford the adducts 9, 14, and 25. The bis-TBS derivatives 10, 15 and 22, upon hydroxylation with catalytic 0804-NMO, yield the differentially protected polyols 11, 16, and 23.

  DOI：

  10.1021/jo00074a004
• 作为产物：
  描述：

  (-)-二甲基-2,3-邻异丙亚基-L-酒石酸酯 在 四氧化锇 、 lithium aluminium tetrahydride 、 N-甲基吲哚酮 、 三氟化硼乙醚 、 sodium hydride 、 二异丁基氢化铝 、 高碘酸 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3S,4S,5S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-5-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4,5-dihydroxy-pentanal
  参考文献：
  名称：

  Stereoselective synthesis of long-chain polyols by sequential homologation of enals with nonracemic .gamma.-silyloxy allylic stannanes and directed hydroxylation

  摘要：

  The nonracemic gamma-silyloxy allylic stannanes (S)-8 and (R)-8 add to the (R,R)-tartrate derived enals 7 and 24 to afford the adducts 9, 14, and 25. The bis-TBS derivatives 10, 15 and 22, upon hydroxylation with catalytic 0804-NMO, yield the differentially protected polyols 11, 16, and 23.

  DOI：

  10.1021/jo00074a004