(4R,5R,6S,7R)-7-tert-butyldimethylsilyloxy-4,6,8-trimethyl-5-[(2S,3S,4R)-1,5-dioxo-2,4-dimethyl-3-hydroxyheptyloxy]non-3-one | 888488-28-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (4R,5R,6S,7R)-7-tert-butyldimethylsilyloxy-4,6,8-trimethyl-5-[(2S,3S,4R)-1,5-dioxo-2,4-dimethyl-3-hydroxyheptyloxy]non-3-one
• 英文别名: [(3R,4S,5R,6R)-3-[tert-butyl(dimethyl)silyl]oxy-2,4,6-trimethyl-7-oxononan-5-yl] (2S,3S,4R)-3-hydroxy-2,4-dimethyl-5-oxoheptanoate
• CAS: 888488-28-6
• 化学式: C₂₇H₅₂O₆Si
• 分子量: 500.792
• InChiKey: OBLAPQUKVOJZHV-ZZCMYJCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5R,6S,7R)-7-tert-butyldimethylsilyloxy-4,6,8-trimethyl-5-[(2S,3S,4R)-1,5-dioxo-2,4-dimethyl-3-hydroxyheptyloxy]non-3-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氘代苯 为溶剂， 生成 (6S,7R)-7-tert-butyldimethylsilyloxy-4,6,8-trimethylnon-4-en-3-one
  参考文献：
  名称：

  A Retro-Claisen Approach to Dolabriferol

  摘要：

  The protected precursor 30 to dolabriferol was generated by a DBU-induced, ester-forming, retro-Claisen process. The required linear carbon chain present in 22 was synthesized by a stereoselective lithium aldol reaction. The necessary aldehyde and ketone fragments were synthesized using stereocontrolled aldol reactions with the ethyl (S)-lactate derived ketone 13.

  DOI：

  10.1021/ol060347s
• 作为产物：
  描述：

  (2S,4R,5R,6R)-2-benzoyloxy-7-benzyloxy-5-hydroxy-4,6-dimethylheptan-3-one 在 W-2 Raney nickel 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 samarium diiodide 、 草酰氯 、 三氟甲磺酸 、 氢气 、 戴斯-马丁氧化剂 、 二甲基亚砜 、 三乙胺 、 tris(dimethylamino)sulfonium trimethylsilyldifluoride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 (4R,5R,6S,7R)-7-tert-butyldimethylsilyloxy-4,6,8-trimethyl-5-[(2S,3S,4R)-1,5-dioxo-2,4-dimethyl-3-hydroxyheptyloxy]non-3-one
  参考文献：
  名称：

  A Retro-Claisen Approach to Dolabriferol

  摘要：

  The protected precursor 30 to dolabriferol was generated by a DBU-induced, ester-forming, retro-Claisen process. The required linear carbon chain present in 22 was synthesized by a stereoselective lithium aldol reaction. The necessary aldehyde and ketone fragments were synthesized using stereocontrolled aldol reactions with the ethyl (S)-lactate derived ketone 13.

  DOI：

  10.1021/ol060347s

文献信息

• A Retro-Claisen Approach to Dolabriferol
  作者：Troy Lister、Michael V. Perkins

  DOI：10.1021/ol060347s

  日期：2006.4.1

  The protected precursor 30 to dolabriferol was generated by a DBU-induced, ester-forming, retro-Claisen process. The required linear carbon chain present in 22 was synthesized by a stereoselective lithium aldol reaction. The necessary aldehyde and ketone fragments were synthesized using stereocontrolled aldol reactions with the ethyl (S)-lactate derived ketone 13.