(4S)-4-Isopropyl-2-methyltetronic acid | 112781-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (4S)-4-Isopropyl-2-methyltetronic acid
• 英文别名: (S)-2-methyl-4-isopropyltetronic acid；(5S)-4-hydroxy-3-methyl-5-(2-propyl)-2(5H)-furanone；(2S)-3-hydroxy-4-methyl-2-propan-2-yl-2H-furan-5-one
• CAS: 112781-32-5
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: YWCUKHVGDPZIOP-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-4-Isopropyl-2-methyltetronic acid 在 W-2 Raney nickel 氢气 作用下， 以 水 为溶剂， 70.0 ℃ 、7.93 MPa 条件下， 反应 40.0h， 以6%的产率得到(2S,3S,4R)-2,3-dihydro-4-isopropyl-2-methyltetronic acid
  参考文献：
  名称：

  双氢精蛋白的合成研究。一世。修订了羟基异戊基丙酰基（hip）单元的立体化学。

  摘要：

  合成和光谱证据的绝对构型中存在于二肽双氢精蛋白中的羟基异戊二酰基丙酰基（HIP）单元的不对称中心。

  DOI：

  10.1016/s0040-4020(01)96067-3
• 作为产物：
  描述：

  (S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,5-dimethyl-3-oxo-hexanoic acid benzyl ester 在 tetrabutylammonium tetrafluoroborate 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以47%的产率得到(4S)-4-Isopropyl-2-methyltetronic acid
  参考文献：
  名称：

  Synthesis of derivatives of (2S,4S)-4-hydroxy-2,5-dimethyl-3-oxohexanoic acid, a constituent of the didemnins

  摘要：

  The syntheses of the two protected derivatives 7 and 16 of (2S,4S)-4-hydroxy-2, 5-dimethyl-3-oxohexanoic acid, a constituent of the didemnin family of antineoplastic macrocyclic depsipeptides are described, The preparation of 7 was carried out by modification of a previously reported synthetic route whereas the use of derivative 16 represents a novel approach to the management of this sub-unit, Removal of the carboxy protecting groups from 7 or 16, followed by amide bond formation with derivatives of(S)-leucine, and oxidation in the cases of compounds deriving from 16, generates the diastereoisomeric intermediates 11, 22 and 23, In each of these either of the protecting groups can be removed in the presence of the other, allowing them to be elaborated further at either terminus, Previous work indicates that diastereoisomeric mixtures of such intermediates can, in principle, be used to obtain optically pure didemnins.

  DOI：

  10.1039/p19960001427

文献信息

• Momose, Takefumi; Toyooka, Naoki; Nishio, Morihiro, Heterocycles, 1999, vol. 51, # 6, p. 1321 - 1343
  作者：Momose, Takefumi、Toyooka, Naoki、Nishio, Morihiro、Shinoda, Hiroyuki、Fujii, Hiromi、Yanagino, Hironobu

  DOI：——

  日期：——
• MOMOSE, TAKEFUMI;TOYOOKA, NAOKI;FUJII, HIROMI;YANAGINO, HIRONOBU, HETEROCYCLES, 29,(1989) N, C. 453-458
  作者：MOMOSE, TAKEFUMI、TOYOOKA, NAOKI、FUJII, HIROMI、YANAGINO, HIRONOBU

  DOI：——

  日期：——
• Synthetic studies of didemnins. i. revision of the stereochemistry of the hydroxyisovalerylpropionyl (hip) unit.
  作者：William R. Ewing、Krishna L. Bhat、Madeleine M. Joullie

  DOI：10.1016/s0040-4020(01)96067-3

  日期：——

  Synthetic and spectral evidence for the absolute configuration of the asymmetric centers of the hydroxyisovalerylpropionyl (HIP) unit present in the depsipeptides didemnins is discussed.

  合成和光谱证据的绝对构型中存在于二肽双氢精蛋白中的羟基异戊二酰基丙酰基（HIP）单元的不对称中心。
• Synthesis of derivatives of (2S,4S)-4-hydroxy-2,5-dimethyl-3-oxohexanoic acid, a constituent of the didemnins
  作者：Isabel González、Gemma Jou、Josep Maria Caba、Fernando Albericio、Paul Lloyd-Williams、Ernest Giralt

  DOI：10.1039/p19960001427

  日期：——

  The syntheses of the two protected derivatives 7 and 16 of (2S,4S)-4-hydroxy-2, 5-dimethyl-3-oxohexanoic acid, a constituent of the didemnin family of antineoplastic macrocyclic depsipeptides are described, The preparation of 7 was carried out by modification of a previously reported synthetic route whereas the use of derivative 16 represents a novel approach to the management of this sub-unit, Removal of the carboxy protecting groups from 7 or 16, followed by amide bond formation with derivatives of(S)-leucine, and oxidation in the cases of compounds deriving from 16, generates the diastereoisomeric intermediates 11, 22 and 23, In each of these either of the protecting groups can be removed in the presence of the other, allowing them to be elaborated further at either terminus, Previous work indicates that diastereoisomeric mixtures of such intermediates can, in principle, be used to obtain optically pure didemnins.