(4S,2'S,3'R)-3-(3'-hydroxy-2'-methylhexanoyl)-4-isopropyl-2-oxazolidinone | 410086-99-6

• 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: (4S,2'S,3'R)-3-(3'-hydroxy-2'-methylhexanoyl)-4-isopropyl-2-oxazolidinone
• 英文别名: (4S)-3-[(2S,3R)-3-hydroxy-2-methylhexanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 410086-99-6
• 化学式: C₁₃H₂₃NO₄
• 分子量: 257.33
• InChiKey: LGUHGTYRJGPZJB-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,2'S,3'R)-3-(3'-hydroxy-2'-methylhexanoyl)-4-isopropyl-2-oxazolidinone 在 吡啶 、 氯化亚砜 、 sodium azide 、 15-冠醚-5 、 lithium hydroxide monohydrate 、 氢气 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 methyl (2S,3S)-3-(benzyloxycarbonylamino)-2-methylhexanoate
  参考文献：
  名称：

  Enantioselective Aldehyde α-Nitroalkylation via Oxidative Organocatalysis

  摘要：

  The first enantioselective organocatalytic alpha-nitroatkylation of aldehydes has been accomplished. The aforementioned process involves the oxidative coupling of an enamine intermediate, generated transiently via condensation of an amine catalyst with an aldehyde, with a silyl. nitronate to produce a beta-nitroaldehyde. Two methods, one that furnishes the syn beta-nitroaldehyde and a second that provides access to the anti isomer, have been developed. Data are presented to support a hypothesis that explains this phenomenon in terms of a silyl group-controlled change in mechanism. Finally, a three-step procedure for the synthesis of both syn- and anti-alpha,beta-disubstituted beta-amino acids is presented.

  DOI：

  10.1021/ja904504j
• 作为产物：
  描述：

  (S)-4-异丙基-3-丙酰基-2-恶唑烷酮 、 正丁醛 在 三氟甲磺酸二丁硼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以84%的产率得到(4S,2'S,3'R)-3-(3'-hydroxy-2'-methylhexanoyl)-4-isopropyl-2-oxazolidinone
  参考文献：
  名称：

  Kulokekahilide-1, a Cytotoxic Depsipeptide from the Cephalaspidean Mollusk Philinopsis speciosa

  摘要：

  The cytotoxic depsipeptide kulokekahilide-1, which contains two unusual amino acids, 4-phenylvaline and 3-amino-2-methylhexanoic acid, was isolated from the cephalaspidean mollusk Philinopsis speciosa. Structure elucidation of kulokekahilide-1 was carried out by spectroscopic analysis and chemical degradation. The absolute stereochemistry was determined by Marfey analysis for amino acids and chiral HPLC analysis for hydroxy acids. All four stereoisomers of 4-phenylvaline and 3-amino-2-methylhexanoic acid, which were necessary for Marfey analysis, were synthesized by use of the Heck reaction and Evans's method, respectively. Kulokekahilide-1 showed cytotoxicity against P388 murine leukemia cells with an IC50 value of 2.1 mug/mL.

  DOI：

  10.1021/jo010176z

文献信息

• Kulokekahilide-1, a Cytotoxic Depsipeptide from the Cephalaspidean Mollusk <i>Philinopsis speciosa</i>
  作者：Junji Kimura、Yuuki Takada、Tomoko Inayoshi、Yoichi Nakao、Gilles Goetz、Wesley Y. Yoshida、Paul J. Scheuer

  DOI：10.1021/jo010176z

  日期：2002.3.1

  The cytotoxic depsipeptide kulokekahilide-1, which contains two unusual amino acids, 4-phenylvaline and 3-amino-2-methylhexanoic acid, was isolated from the cephalaspidean mollusk Philinopsis speciosa. Structure elucidation of kulokekahilide-1 was carried out by spectroscopic analysis and chemical degradation. The absolute stereochemistry was determined by Marfey analysis for amino acids and chiral HPLC analysis for hydroxy acids. All four stereoisomers of 4-phenylvaline and 3-amino-2-methylhexanoic acid, which were necessary for Marfey analysis, were synthesized by use of the Heck reaction and Evans's method, respectively. Kulokekahilide-1 showed cytotoxicity against P388 murine leukemia cells with an IC50 value of 2.1 mug/mL.
• Enantioselective Aldehyde α-Nitroalkylation via Oxidative Organocatalysis
  作者：Jonathan E. Wilson、Anthony D. Casarez、David W. C. MacMillan

  DOI：10.1021/ja904504j

  日期：2009.8.19

  The first enantioselective organocatalytic alpha-nitroatkylation of aldehydes has been accomplished. The aforementioned process involves the oxidative coupling of an enamine intermediate, generated transiently via condensation of an amine catalyst with an aldehyde, with a silyl. nitronate to produce a beta-nitroaldehyde. Two methods, one that furnishes the syn beta-nitroaldehyde and a second that provides access to the anti isomer, have been developed. Data are presented to support a hypothesis that explains this phenomenon in terms of a silyl group-controlled change in mechanism. Finally, a three-step procedure for the synthesis of both syn- and anti-alpha,beta-disubstituted beta-amino acids is presented.