4-(R)-benzyl-3-[(2R,3S,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-propionyloxy-2,4-dimethylheptanoyl]-oxazolidin-2-one | 623927-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-(R)-benzyl-3-[(2R,3S,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-propionyloxy-2,4-dimethylheptanoyl]-oxazolidin-2-one
• 英文别名: [(2R,3S,4R,5R)-1-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-5-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethyl-1-oxoheptan-3-yl] propanoate
• CAS: 623927-76-4
• 化学式: C₂₈H₄₅NO₆Si
• 分子量: 519.754
• InChiKey: IGXVJIJJORMOCD-HSULDRTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(R)-benzyl-3-[(2R,3S,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-propionyloxy-2,4-dimethylheptanoyl]-oxazolidin-2-one 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以58%的产率得到(5R,6S)-6-[(1S,2R)-2-(tert-butyldimethylsilanyloxy)-1-methylbutyl]-4-hydroxy-3,5-dimethyl-5,6-dihydropyran-2-one
  参考文献：
  名称：

  Substrate Recognition and Channeling of Monomodules from the Pikromycin Polyketide Synthase

  摘要：

  The unique ability of the pikromycin (Pik) polyketide synthase to generate 12- and 14-membered ring macrolactones presents an opportunity to explore the fundamental processes underlying polyketide synthesis, specifically the mechanistic details of the chain extension process. We have overexpressed and purified PikAIII (module 5) and PikAIV (module 6) and assessed the ability of these proteins to generate tri- and tetraketide lactone products using N-acetylcysteamine-activated diketides and C-14-methylmalonyl-CoA as substrates. Comparison of the stereochemical specificities for PikAIII and PikAIV and the reported values for the DEBS modules reveals significant differences between these systems.

  DOI：

  10.1021/ja034841s
• 作为产物：
  描述：

  (4R,2'R,3'S,4'S)-3-(2',4'-dimethyl-3',5'-dihydroxyheptanoyl)-4-benzyl-2-oxazolidinone 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.08h， 生成 4-(R)-benzyl-3-[(2R,3S,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-propionyloxy-2,4-dimethylheptanoyl]-oxazolidin-2-one
  参考文献：
  名称：

  Substrate Recognition and Channeling of Monomodules from the Pikromycin Polyketide Synthase

  摘要：

  The unique ability of the pikromycin (Pik) polyketide synthase to generate 12- and 14-membered ring macrolactones presents an opportunity to explore the fundamental processes underlying polyketide synthesis, specifically the mechanistic details of the chain extension process. We have overexpressed and purified PikAIII (module 5) and PikAIV (module 6) and assessed the ability of these proteins to generate tri- and tetraketide lactone products using N-acetylcysteamine-activated diketides and C-14-methylmalonyl-CoA as substrates. Comparison of the stereochemical specificities for PikAIII and PikAIV and the reported values for the DEBS modules reveals significant differences between these systems.

  DOI：

  10.1021/ja034841s