(2S,3S)-2-羟基-3-({[(2-甲基-2-丙基)氧基]羰基}氨基)-3-苯丙酸 | 59937-41-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: (2S,3S)-2-羟基-3-({[(2-甲基-2-丙基)氧基]羰基}氨基)-3-苯丙酸
• 英文名称: (2S,3S)-3-((tert-Butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoic acid
• 英文别名: (2S,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid
• CAS: 59937-41-6
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: ZVAFCKLQJCZGAP-QWRGUYRKSA-N

物化性质

• 沸点：
  470.4±45.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (2S,3S)-2-羟基-3-({[(2-甲基-2-丙基)氧基]羰基}氨基)-3-苯丙酸 以 乙醚 为溶剂， 以49.0 mg的产率得到甲基(2S,3S)-N-boc-3-苯基异丝氨酸盐酸
  参考文献：
  名称：

  Totally Stereocontrolled Nitrone−Ketene Acetal Based Synthesis of (2S,3S)-N-Benzoyl- and N-Boc-phenylisoserine

  摘要：

  A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N-benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.

  DOI：

  10.1021/jo971009v
• 作为产物：
  描述：

  [(1R,2S)-2-phenylcyclohexyl] (2S,3S)-3-[[tert-butyl(dimethyl)silyl]oxy-[(1R)-1-phenylethyl]amino]-3-phenyl-2-triethylsilyloxypropanoate 在 palladium dihydroxide 氢氟酸 、 氢气 、 三乙胺 作用下， 以 溶剂黄146 为溶剂， 生成 (2S,3S)-2-羟基-3-({[(2-甲基-2-丙基)氧基]羰基}氨基)-3-苯丙酸
  参考文献：
  名称：

  Totally Stereocontrolled Nitrone−Ketene Acetal Based Synthesis of (2S,3S)-N-Benzoyl- and N-Boc-phenylisoserine

  摘要：

  A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N-benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.

  DOI：

  10.1021/jo971009v

文献信息

• Process for the preparation of taxane derivatives
  申请人：Aventis Pharma S.A.

  公开号：US20030013889A1

  公开（公告）日：2003-01-16

  Taxane derivatives and a method of preparing taxane derivatives of formula (I): 1 are disclosed. In general formula (I), Ar represents an aryl radical; R represents a phenyl radical or a radical R 5 —O— in which R 5 represents an alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or saturated or unsaturated nitrogenous heterocylcyl radical, R 1 and R 2 , which are identical or different, each represent a hydrogen atom or an alkyl, phenylalkyl, phenyl, alkoxyphenyl, or dialkoxyphenyl radical, or else R 1 and R 2 form, together with the carbon atom to which they are bonded, a ring having from 4 to 7 members; R 3 represents an acetyl radical or a protecting group of the hydroxyl functional group; and R 4 represents a protecting group of the hydroxyl functional group.

  本文揭示了紫杉烷衍生物以及制备通式（I）1的方法。在通式（I）中，Ar代表芳基基团；R代表苯基团或基团R5-O-，其中R5代表烷基，烯基，炔基，环烷基，苯基或饱和或不饱和氮杂环基团，R1和R2相同或不同，每个代表氢原子或烷基，苯基烷基，苯基，烷氧基苯基或二烷氧基苯基基团，或者R1和R2与它们连接的碳原子一起形成具有4至7个成员的环；R3表示乙酰基基团或羟基官能团的保护基团；R4表示羟基官能团的保护基团。
• US5686623A
  申请人：——

  公开号：US5686623A

  公开（公告）日：1997-11-11
• US6433180B1
  申请人：——

  公开号：US6433180B1

  公开（公告）日：2002-08-13
• Totally Stereocontrolled Nitrone−Ketene Acetal Based Synthesis of (2<i>S</i>,3<i>S</i>)-<i>N</i>-Benzoyl- and <i>N</i>-Boc-phenylisoserine
  作者：Sylvie Jost、Yves Gimbert、Andrew E. Greene、Frédéric Fotiadu

  DOI：10.1021/jo971009v

  日期：1997.9.1

  A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N-benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.