(3S)-1-<(S)-Phenylethyl>-5-methoxy-3-hydroxy-3-methylglutaroamide | 147802-41-3

• 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: (3S)-1-<(S)-Phenylethyl>-5-methoxy-3-hydroxy-3-methylglutaroamide
• 英文别名: methyl (3S)-3-hydroxy-3-methyl-5-oxo-5-[[(1S)-1-phenylethyl]amino]pentanoate
• CAS: 147802-41-3
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: NYCXDKQKYXENFQ-NHYWBVRUSA-N

物化性质

• 沸点：
  484.1±45.0 °C(predicted)
• 密度：
  1.137±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S)-1-<(S)-Phenylethyl>-5-methoxy-3-hydroxy-3-methylglutaroamide 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 生成 (3R)-1-[(S)-1-phenylethyl]mevalonamide
  参考文献：
  名称：

  一种用于制备手性HMGA（3-羟基-3-甲基戊二酸）酯和酰胺的新试剂。HMGA酸酐的不对称脱对称合成（R）-和（S）-β-羧甲基-β-甲基-β-内酯

  摘要：

  （R）-和（S）-β-羧甲基-β-甲基-β-内酯通过HMGA的不对称脱对称作用开发了用于制备手性HMGA（3-羟基-3-甲基戊二酸）酯和酰胺的新试剂酐。使试剂与各种醇盐平稳反应，而无需外消旋作用，得到所需的半酯。另一方面，在回流的甲苯中与各种胺的反应得到外消旋酰胺。使用试剂的相应甲酯制备了手性HMGA酰胺。

  DOI：

  10.1016/0040-4039(96)00274-2
• 作为产物：
  描述：

  3-羟基-3-甲基谷氨酸 在 正丁基锂 、 N,N'-二环己基碳二亚胺 、 氢化奎宁 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醚 为溶剂， 反应 2.5h， 生成 (3S)-1-<(S)-Phenylethyl>-5-methoxy-3-hydroxy-3-methylglutaroamide
  参考文献：
  名称：

  一种用于制备手性HMGA（3-羟基-3-甲基戊二酸）酯和酰胺的新试剂。HMGA酸酐的不对称脱对称合成（R）-和（S）-β-羧甲基-β-甲基-β-内酯

  摘要：

  （R）-和（S）-β-羧甲基-β-甲基-β-内酯通过HMGA的不对称脱对称作用开发了用于制备手性HMGA（3-羟基-3-甲基戊二酸）酯和酰胺的新试剂酐。使试剂与各种醇盐平稳反应，而无需外消旋作用，得到所需的半酯。另一方面，在回流的甲苯中与各种胺的反应得到外消旋酰胺。使用试剂的相应甲酯制备了手性HMGA酰胺。

  DOI：

  10.1016/0040-4039(96)00274-2

文献信息

• Three novel furospirostanol glycosides and a steroidal alkaloid glycoside from the bulbs of <i>Fritillaria camtschatcensis</i> (L.) Ker Gawl., and their cytotoxicity
  作者：Tomoki Iguchi、Minpei Kuroda、Hiroshi Takayama、Yoshihiro Mimaki

  DOI：10.1080/14786419.2021.1897590

  日期：2022.8.3

  Abstract Three novel steroidal glycosides (1–3) and a previously described steroidal alkaloid glycoside (4) have been isolated from the bulbs of Fritillaria camtschatcensis (L.) Ker Gawl. (Liliaceae). The structures of novel compounds 1–3 were characterized based on NMR spectroscopy and chemical transformations. Compounds 1–3 are furospirostanol glycosides bearing a (3S)-3-hydroxy-3-methylglutaryl

  摘要 从贝母(L.) Ker Gawl的鳞茎中分离出三种新型甾体苷 ( 1-3 )和一种先前描述的甾体生物碱苷 ( 4 )。（百合科）。新型化合物1-3的结构基于 NMR 光谱和化学转化进行了表征。化合物1-3是呋螺甾烷醇糖苷，在糖苷配基的 C-26 处带有 (3 S ) -3-羟基-3-甲基戊二酰基部分。化合物1 – 4评估了它们对 HL-60 人早幼粒细胞白血病细胞、A549 人肺腺癌细胞和 SBC-3 人肺小细胞癌细胞的细胞毒活性。只有4 个对 HL-60、A549 和 SBC-3 细胞显示出中等的细胞毒性，IC 50值分别为 22.9、13.3 和 11.9 µM。发现化合物4在 HL-60 细胞中引起坏死样细胞死亡。
• Steroidal saponins from the bulbs of Lilium regale and L. henryi
  作者：Yoshihiro Mimaki、Yutaka Sashida、Osamu Nakamura、Tamotsu Nikaido、Taichi Ohmoto

  DOI：10.1016/0031-9422(93)85472-4

  日期：1993.6

  Two new and three known steroidal saponins were isolated from the fresh bulbs of Lilium regale and two known saponins from those of L. henryi. The structures of the new saponins were established by extensive spectral data, hydrolysis and chemical correlation as (25R)-27-O-[(S)-3-hydroxy-3-methylglutaroyl]-spirost-5 -ene-3 beta,27-diol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->3)]-

  从百合的新鲜鳞茎中分离出两种新的和三种已知的甾体皂苷，从百合的鳞茎中分离出两种已知的皂苷。通过广泛的光谱数据、水解和化学相关性确定了新皂苷的结构为 (25R)-27-O-[(S)-3-羟基-3-甲基戊二酰基]-spirost-5-ene-3 beta,27 -二醇 3-O-α-L-吡喃鼠李糖基-(1-->2)-O-[β-D-吡喃葡萄糖基-(1-->3)]-β-D-吡喃葡萄糖苷和 (25S)-spirost- 5-ene-3 beta,17 alpha,27-triol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-O-[beta-D-glupyranosyl-(1-->2)-O- β-D-吡喃葡萄糖基-(1-->4)]-β-D-吡喃葡萄糖苷。评估了皂苷对环 AMP 磷酸二酯酶的抑制活性。
• Steroidal saponins from the bulbs of Allium schubertii
  作者：Kazuhiro Kawashima、Yoshihiro Mimaki、Yutaka Sashida

  DOI：10.1016/s0031-9422(00)95103-3

  日期：1993.3

  Phytochemical examination of the fresh bulbs of Allium schubertii led to the isolation of four new steroidal saponins together with a known saponin. The structures of the new saponins were established by spectroscopic data, hydrolysis and chemical correlation as (25R and S)-5alpha-spirostan-2alpha,3beta,6beta-triol 3-O-beta-D-glucopyranosyl-(1-->2)-O-[4-O-benzoyl-beta-D-Xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside, (25R and S)-5alpha-spirostan-2alpha,3beta,6beta-triol 3-O-beta-D-glucopyranosyl-(1-->2)-O-[3-O-benzoyl-beta-D-Xylopyranosyl-(1-->3)]-O-beta-D-glu-copyranosyl-(1-->4)-beta-D-galactopyranoside, (25R and S)-5alpha-spirostan-2alpha,3beta,6beta-triol 3-O-beta-D-glucopyranosyl-(1 --> 2)-O-[4-O-(3S)-3-hydroxy-3-methylglutaroyl-beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside and 26-O-beta-D-glucopyranosyl-(25R and S)-5alpha-furostan-2alpha,3beta,6beta,22xi,26-pentol 3-O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside, respectively.
• A new reagent for the preparation of chiral HMGA (3-hydroxy-3-methylglutaric acid) esters and amides. Synthesis of (R)- and (S)-β-carboxymethyl-β-methyl-β-lactones by asymmetric desymmetrization of HMGA anhydride
  作者：Kimiko Hashimoto、Jun-ichi Kitaguchi、Yasuhiro Mizuno、Tadao Kobayashi、Haruhisa Shirahama

  DOI：10.1016/0040-4039(96)00274-2

  日期：1996.3

  (R)- and (S)-β-carboxymethyl-β-methyl-β-lactones, new reagents for the preparation of chiral HMGA (3-hydroxy-3-methylglutaric acid) esters and amides were developed through the asymmetric desymmetrization of HMGA anhydride. The reagent was smoothly reacted with various alkoxide without racemization to afford the desirable half-esters. On the other hand, the reaction with various amine in refluxing

  （R）-和（S）-β-羧甲基-β-甲基-β-内酯通过HMGA的不对称脱对称作用开发了用于制备手性HMGA（3-羟基-3-甲基戊二酸）酯和酰胺的新试剂酐。使试剂与各种醇盐平稳反应，而无需外消旋作用，得到所需的半酯。另一方面，在回流的甲苯中与各种胺的反应得到外消旋酰胺。使用试剂的相应甲酯制备了手性HMGA酰胺。