tert-butyl (3S)-5-hydroxy-3-(hydroxymethyl)pentanoate | 150932-68-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl (3S)-5-hydroxy-3-(hydroxymethyl)pentanoate
• CAS: 150932-68-6
• 化学式: C₁₀H₂₀O₄
• 分子量: 204.266
• InChiKey: ZTBMTAGCMCRXOW-QMMMGPOBSA-N

物化性质

• 沸点：
  314.3±32.0 °C(predicted)
• 密度：
  1.060±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S)-5-hydroxy-3-(hydroxymethyl)pentanoate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (S)-3-Formyl-5-oxo-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  伏马毒素B 2的三碳烯酸部分的绝对构型

  摘要：

  在伏马菌素B的两个丙三羧酸部分的手性中心的构型2被示出为[R 。这种立体化学与其他人最近提出的伏马菌素B 1和AAL毒素T A的三碳烯酸部分相反。

  DOI：

  10.1016/0040-4039(95)00852-4
• 作为产物：
  描述：

  tert-butyl (2E,4E)-2,4-hexadienoate 在 正丁基锂 、 臭氧 作用下， 以 四氢呋喃 为溶剂， 反应 0.52h， 生成 tert-butyl (3S)-5-hydroxy-3-(hydroxymethyl)pentanoate
  参考文献：
  名称：

  Asymmetric conjugate additions of chiral allyl- and crotylphosphonamide anions to .alpha.,.beta.-unsaturated carbonyl compounds: highly stereocontrolled access to vicinally substituted carbon centers and chemically asymmetrized chirons

  摘要：

  Reactions of anions derived from chiral nonracemic allyl and crotyl bicyclic phosphonamides with alpha,beta-unsaturated cyclic ketones, esters, lactones, and lactams take place at the gamma-position of the reagents and lead to diastereomerically pure or highly enriched products of conjugate addition. The option to quench the corresponding enolates with various alkyl halides offers a versatile approach to vicinal substitution including the generation of quaternary carbon centers.

  DOI：

  10.1021/jo00071a004

文献信息

• Combined Synthetic/CD Strategy for the Stereochemical Assignment of the Tricarballylic Acid Side Chains of Fumonisin B₁
  作者：Michaela Hartl、Hans-Ulrich Humpf

  DOI：10.1021/jo0000630

  日期：2001.6.1

  The circular dichroism (CD) exciton chirality method was employed for the stereochemical assignment of the tricarballylic acid (TCA) side chains of fumonisin B(1) 1a (FB(1)). Using 2-naphthoate for chromophoric derivatization of the reduced TCA moieties, the absolute configuration was shown to be R. For additional confirmation, an optically active dihydroxy-tert-butanoate 2 related to the TCA group

  圆二色性（CD）激子手性方法用于伏马菌素B（1）1a（FB（1））的三碳烯酸（TCA）侧链的立体化学分配。使用2-萘甲酸酯还原的TCA部分发色衍生化，绝对构型显示为R。为进一步确认，与伏马菌素B（1）的TCA基团相关的旋光二羟基叔丁酸酯2作为模型化合物。
• Asymmetric conjugate additions of chiral allyl- and crotylphosphonamide anions to .alpha.,.beta.-unsaturated carbonyl compounds: highly stereocontrolled access to vicinally substituted carbon centers and chemically asymmetrized chirons
  作者：Stephen Hanessian、Arthur Gomtsyan、Andrew Payne、Yolande Herve、Serge Beaudoin

  DOI：10.1021/jo00071a004

  日期：1993.9

  Reactions of anions derived from chiral nonracemic allyl and crotyl bicyclic phosphonamides with alpha,beta-unsaturated cyclic ketones, esters, lactones, and lactams take place at the gamma-position of the reagents and lead to diastereomerically pure or highly enriched products of conjugate addition. The option to quench the corresponding enolates with various alkyl halides offers a versatile approach to vicinal substitution including the generation of quaternary carbon centers.
• Absolute configuration at the tricarballylic acid moieties of fumonisin B2
  作者：Craig D Boyle、Yoshito Kishi

  DOI：10.1016/0040-4039(95)00852-4

  日期：1995.6

  The configuration at the chiral centers of the two tricarballylic acid moieties of fumonisin B2 is shown to be R. This stereochemistry is opposite to that recently suggested by others for the tricarballylic acid portions of fumonisin B1 and AAL toxin TA.

  在伏马菌素B的两个丙三羧酸部分的手性中心的构型2被示出为[R 。这种立体化学与其他人最近提出的伏马菌素B 1和AAL毒素T A的三碳烯酸部分相反。