(1R,2S)-(-)-2-Methyl-3-[(4R)-isopropyl-2-oxazolidin-3-yl]-3-oxo-1-(prop-2-enyl)propyll-2-(diphenylphosphanyl)benzoate | 252201-54-0

• 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: (1R,2S)-(-)-2-Methyl-3-[(4R)-isopropyl-2-oxazolidin-3-yl]-3-oxo-1-(prop-2-enyl)propyll-2-(diphenylphosphanyl)benzoate
• 英文别名: [(3R,4S)-2,4-dimethyl-5-oxo-5-[(4R)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]pent-1-en-3-yl] 2-diphenylphosphanylbenzoate
• CAS: 252201-54-0
• 化学式: C₃₂H₃₄NO₅P
• 分子量: 543.599
• InChiKey: QLEJUQBVPIGWID-HTZJHERLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S)-(-)-2-Methyl-3-[(4R)-isopropyl-2-oxazolidin-3-yl]-3-oxo-1-(prop-2-enyl)propyll-2-(diphenylphosphanyl)benzoate 在 acetylacetonatodicarbonylrhodium(l) 亚磷酸三苯酯 、 正丁基锂 、 氢气 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 20.0~90.0 ℃ 、2.0 MPa 条件下， 生成 ethyl E-(5R,6S,7S)-(-)-5,7-dimethyl-6-[2-(diphenylphosphanyl)benzoyloxy]-8-[(4R)-isopropyl-2-oxazolidin-3-yl]oct-2-enoate
  参考文献：
  名称：

  非环戊酸酯中的邻二苯基膦基苯甲酰基定向的铜酸酯。

  摘要：

  用一块石头杀死两只鸟。邻二苯基膦基苯甲酰基（o-DPPB）在立体选择性Rh催化的加氢甲酰化反应中充当催化剂导向基团，在吉尔曼铜酸盐向无环烯酸酯的立体选择性1,4-加成反应中用作试剂导向基团（见右图; o-DPPB基团由一个球体表示，D =施主。这两个反应可以有效地用作合成序列的一部分。

  DOI：

  10.1002/(sici)1521-3773(19980302)37:4<525::aid-anie525>3.0.co;2-m
• 作为产物：
  描述：

  2-二苯基膦苯甲酸 、 (R)-3-((2S,3R)-3-Hydroxy-2,4-dimethyl-pent-4-enoyl)-4-isopropyl-oxazolidin-2-one 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以55%的产率得到(1R,2S)-(-)-2-Methyl-3-[(4R)-isopropyl-2-oxazolidin-3-yl]-3-oxo-1-(prop-2-enyl)propyll-2-(diphenylphosphanyl)benzoate
  参考文献：
  名称：

  Substrate-Directed Diastereoselective Hydroformylation: Key Step for the Assembly of Polypropionate Subunits

  摘要：

  Stereoselective hydroformylation of methallylic alcohols of types 3 and 4, that employed the substrate-bound catalyst-directing ortho-diphenyl-phosphanylbenzoyl (o-DPPB) group, was used as a key step for the construction of bifunctionalized stereotriads, which ale central building blocks of polyketide natural products. The required diastereomerically pure syn- and anti- starting methallylic alcohol systems 3 and 4 were obtained either by Cram-selective carbonyl reduction, Frater alkylation, or by chelation-controlled carbonyl reduction. Enantiomerically pure stereotriad building blocks were derived from a combination of an Evans aldol addition and subsequent o-DPPB-directed stereoselective hydroformylation (-->24). A crystal structure analysis for steretriad building block 24 confirmed the relative and absolute configuration of the stereogenic centers. Additionally, it provided evidence for a previously postulated preferred conformation of the catalyst-directing o-DPPB group as well as of the polyketide main chain.

  DOI：

  10.1002/(sici)1521-3765(19991001)5:10<2819::aid-chem2819>3.0.co;2-z