(2S,3R)-2,3-epoxy-2-methylbutanoic acid | 499971-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2S,3R)-2,3-epoxy-2-methylbutanoic acid
• 英文别名: (2S,3R)-2,3-epoxyangelic acid；(2S,3R)-2,3-dimethyloxirane-2-carboxylic acid
• CAS: 499971-91-4
• 化学式: C₅H₈O₃
• 分子量: 116.117
• InChiKey: YTQMZWQQWSTMDQ-WUJLRWPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7β-hydroxy-9α-angeloyloxy-1-oxolongipin-2-ene 、 (2S,3R)-2,3-epoxy-2-methylbutanoic acid 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 48.0h， 以69%的产率得到9α-angeloyloxy-7β-<(2S,3R)-2,3-epoxy-2-methylbutyryloxy>-1-oxolongipin-2-ene
  参考文献：
  名称：

  （2 R，3 S）-（-）-和（2 S，3 R）-（+）-2,3-环氧-2-甲基丁酸及其酯的制备

  摘要：

  由2-甲基-2-丁烯酸制备对映体纯的（2 R，3 S）-（-）-和（2 S，3 R）-（+）-2,3-环氧-2-甲基丁酸7和8。酸1（tiglic酸）。通过光谱和光学活性数据对其进行了表征，并通过与（R）-（+）-和（S）-（-）-2-甲基-1,2-丁二醇的化学相关性确定了它们的绝对构型。相应的甲基（16和17），薄荷基（3和4）和9α-Angylyloxy-1-oxolongipin-2-en-7β-yl（14和还制备了15）酯。

  DOI：

  10.1016/0957-4166(95)00205-4
• 作为产物：
  描述：

  (E)-2-甲基-2-丁烯酰氯 在 盐酸 、 氢氧化钾 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (2S,3R)-2,3-epoxy-2-methylbutanoic acid
  参考文献：
  名称：

  （2 R，3 S）-（-）-和（2 S，3 R）-（+）-2,3-环氧-2-甲基丁酸及其酯的制备

  摘要：

  由2-甲基-2-丁烯酸制备对映体纯的（2 R，3 S）-（-）-和（2 S，3 R）-（+）-2,3-环氧-2-甲基丁酸7和8。酸1（tiglic酸）。通过光谱和光学活性数据对其进行了表征，并通过与（R）-（+）-和（S）-（-）-2-甲基-1,2-丁二醇的化学相关性确定了它们的绝对构型。相应的甲基（16和17），薄荷基（3和4）和9α-Angylyloxy-1-oxolongipin-2-en-7β-yl（14和还制备了15）酯。

  DOI：

  10.1016/0957-4166(95)00205-4

文献信息

• New ent-kaurane diterpenes with chiral epoxyangelate moieties from Wedelia prostrata
  作者：Zhongnan Wu、Yubo Zhang、Wen Li、Nenghua Chen、Qianwen Niu、Yingying Li、Qingguo Li、Dan Yang、Yaolan Li、Guocai Wang

  DOI：10.1016/j.cclet.2018.05.038

  日期：2019.2

  (2), (2′S,3′R)-3α-(2′,3′-epoxyangeloyloxy)-kaur-16-en-19-oic acid (3) and (2′R,3′S)-3α-(2′,3′-epoxyangeloyloxy)-kaur-16-en-19-oic acid (4), along with eight known diterpenes (5−12), were isolated from Wedelia prostrata. The absolute configurations of the new structures were determined by X-ray crystallography, ECD calculations and chemical methods. All compounds were evaluated for their cytotoxicity

  摘要四个新的手性环氧天使酸酯新的对映月桂烷二萜，（2'R，3'R）-3α-（2'，3'-epoxyangeloyloxy）-kaur-16-en-19-oic acid（1），（2 ′S，3′S）-3α-（2′，3′-环氧angylyloxy）-kaur-16-en-19-oic acid（2），（2′S，3′R）-3α-（2′， 3'-环氧Angeloyloxy）-kaur-16-en-19-oic酸（3）和（2'R，3'S）-3α-（2'，3'-epoxyangeloyloxy）-kaur-16-en-19-从Wedelia prostrata中分离出了油酸（4）和八种已知的二萜（5-12）。新结构的绝对构型是通过X射线晶体学，ECD计算和化学方法确定的。评估了所有化合物对人HepG-2细胞的细胞毒性活性，IC50值为11.72±0.22μmol/ L至54.75±1.12μmol/ L。
• Synthesis, isolation, stereostructure and cytotoxicity of paclitaxel analogs from cephalomannine
  作者：Feng Gao、Dan Wang、Xing Huang

  DOI：10.1016/j.fitote.2013.07.011

  日期：2013.10

  Four paclitaxel derivatives were afforded by preparative HPLC separation of two pairs of diastereoisomers, which were obtained by catalytic hydrogenation and epoxidation of the C-13 side-chain double bond of cephalomannine, a naturally occurring paclitaxel analog. The four paclitaxel derivatives were analyzed using NMR, CD spectroscopy, and side-chain hydrolysis in order to measure their optical rotations and GC characteristics. In this way, the stereoconfigurations of the products were determined. Evaluation of the compounds' activity indicated that they had differing cytotoxic activities: compound 5 had superior activity in BCG-823 tumor cells compared to paclitaxel, while compound 7 had superior activity in HCT-8 and A549 tumor cells compared to paclitaxel. These results indicate that the stereoconfiguration of the paclitaxel N-acyl side chain has a significant impact on its activity. (C) 2013 Elsevier B.V. All rights reserved.
• Absolute configuration of longipinenyl epoxyangelates from three Stevia species
  作者：J Martn Torres-Valencia、Carlos M Cerda-Garca-Rojas、Luisa U Román、Juan D Hernández、Pedro Joseph-Nathan

  DOI：10.1016/s0031-9422(98)00304-5

  日期：1998.12

  The complete stereostructures of two longipinene derivatives-from three Stevia species, which contain chiral epoxyangelate moieties are assigned as (4R,5S,7R,9R,10R,11R,2'R,3'R)- and (4R,5S,7R,9R,10R,11R,2'S,3'S)-9-angeloyloxy-7-(2',3'-epoxy-2'-methylbutyryloxy)-1-oxolongipin-2-ene. These results follow from the preparation of the substances by incorporation of both enantiomers of epoxyangelic acid into 9-angeloyloxy-7-hydroxy-1-oxolongipin-2-ene, followed by comparison of the N-1 NMR data of the prepared esters with those of the natural substances. Minimum energy structures for both compounds using molecular mechanics calculations are also reported. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Preparation of (2R,3S)-(−)- and (2S,3R)-(+)-2,3-epoxy-2-methylbutanoic acids and some of their esters
  作者：J Martín Torres-Valencia、Carlos M Cerda-García-Rojas、Pedro Joseph-Nathan

  DOI：10.1016/0957-4166(95)00205-4

  日期：1995.7

  Enantiomerically pure (2R,3S)-(−)- and (2S,3R)-(+)-2,3-epoxy-2-methylbutanoic acids 7 and 8 were prepared from 2-methyl-2-butenoic acid 1 (tiglic acid). They were characterized by spectroscopic and optical activity data and their absolute configuration was determined by chemical correlation with (R)-(+)- and (S)-(−)-2-methyl-1,2-butanediols. The corresponding methyl (16 and 17), menthyl (3 and 4),

  由2-甲基-2-丁烯酸制备对映体纯的（2 R，3 S）-（-）-和（2 S，3 R）-（+）-2,3-环氧-2-甲基丁酸7和8。酸1（tiglic酸）。通过光谱和光学活性数据对其进行了表征，并通过与（R）-（+）-和（S）-（-）-2-甲基-1,2-丁二醇的化学相关性确定了它们的绝对构型。相应的甲基（16和17），薄荷基（3和4）和9α-Angylyloxy-1-oxolongipin-2-en-7β-yl（14和还制备了15）酯。