monomethyl (S)-3-hydroxy-3-methylglutarate | 56652-40-5

• 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: monomethyl (S)-3-hydroxy-3-methylglutarate
• 英文别名: (3S)-3-hydroxy-5-methoxy-3-methyl-5-oxopentanoic acid
• CAS: 56652-40-5
• 化学式: C₇H₁₂O₅
• 分子量: 176.169
• InChiKey: UNHGPASVFNKZNR-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  monomethyl (S)-3-hydroxy-3-methylglutarate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以7.2 mg的产率得到D-甲瓦龙酸?酯
  参考文献：
  名称：

  Steroidal glycosides from Allium albopilosum and A. ostrowskianum

  摘要：

  Chemical studies of the bulbs of Allium albopilosum and A. ostrowskianum have led to the isolation of two new steroidal saponins and four new cholestane glycosides together with several known compounds. The structures of the new compounds were established by the spectroscopic data, hydrolysis and chemical correlations as (25 R and S)-5alpha-spirostane-2alpha,3beta,6beta-triol 3-O-{O-beta-D-glucopyranosyl-(1-->2)-O-[3-O-acetyl-beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside}, (25R)-2-O-[(S)-3-hydroxy-3-methylglutaroyl]-5alpha-spirostane-2alpha,3beta,6beta-triol 3-O-{O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-Xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-d-galactopyranoside}, (22S)-cholest-5-ene-1beta,3beta,16beta,22-tetraol 1-O-alpha-L-rhamnopyranoside 16-O-{O-alpha-L-rhamnopyr-anosyl-(1-->3)-beta-D-glucopyranoside), 1beta,3beta,16beta-trihydroxycholest-5-en-22-one 1-O-alpha-L-rhamnopyranoside 16-O-{O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-glucopyranoside}, 1beta,3beta,16beta-trihydroxy-5alpha-cholestan-22-one 1-O-alpha-L-rhamnopyranoside 16-O-{O-alpha-L-rhamnopyranosYl-(1-->3)-beta-D-glucopyranoside} and (22S)-cholest-5-ene-1beta,3beta,16beta,22-tetraol 16-O-{O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranoside}.

  DOI：

  10.1016/0031-9422(93)85362-u
• 作为产物：
  描述：

  3-羟基-3-甲基戊二酸二甲酯 在 pig liver esterase 作用下， 以 phosphate buffer 为溶剂， 以92%的产率得到monomethyl (S)-3-hydroxy-3-methylglutarate
  参考文献：
  名称：

  Stereoselective total syntheses of atrochrysone, torosachrysone and related 3,4-dihydroanthracen-1(2H )-ones

  摘要：

  本文介绍了两种对映体形式的前蒽醌类化合物阿托品酮 1 和托罗品酮 2 的全合成方法。该合成依赖于手性二酯的区域选择性特贝甲烯化，然后与 N-三氟甲基-4-（二甲基氨基）吡啶三酸酯进行分子内烯醚酰化。得到的 3-甲氧基环己-2-烯酮 9 与合适的奥塞林酸衍生物缩合，经脱保护后得到具有光学活性的 3,4-二氢蒽-1(2H)-酮 1 和 2。这种灵活的方法可用于合成 13C 标记的化合物，并可获得一系列类似物。

  DOI：

  10.1039/b003053h

文献信息

• A Study of Stereoselective Hydrolysis of Symmetrical Diesters with Pig Liver Esterase
  作者：Peter Mohr、Nada Waespe-?ar?evi?、Christoph Tamm、Krystyna Gawronska、Jacek K. Gawronski

  DOI：10.1002/hlca.19830660815

  日期：1983.12.14

  Pig liver esterase-(PLE) catalyzed hydrolysis of dimethyl esters of symmetrical dicarboxylic acids, including meso-diacids, cis-1,2-cycloalkanedicarboxylic acids, and diacids with a prochiral center, was studied with 14 substrates. The products of these stereoselective hydrolyses are chiral monoesters of dicarboxylic acids, with an enantiomeric excess (e.e.) from 10% to 100%. Some of these optically

  猪肝esterase-（PLE）的对称的二羧酸，其中包括二甲基酯的催化水解内消旋-diacids，顺式-1,2-环烷烃酸，并用前手性中心二酸，用14个基板研究。这些立体选择性水解的产物是二元羧酸的手性单酯，对映体过量（ee）为10％至100％。这些光学活性单酯中的一些是天然产物合成中有价值的合成子。
• Catalytic asymmetric induction from prochiral cyclic acid anhydrides using cinchona alkaloids
  作者：Jun Hiratake、Yukio Yamamoto、Jun'ichi Oda

  DOI：10.1039/c39850001717

  日期：——

  Asymmetric ring-opening of prochiral cyclic acid anhydrides (1) with methanol was effected by a catalytic amount of cinchona alkaloids (2) with an enantiomeric excess of up to 70% and the product was converted into optically active lactones.

  前手性环状酸酐（1）与甲醇的不对称开环是通过催化量的金鸡纳生物碱（2）的对映体过量最高达70％进行的，产物转化为旋光内酯。
• 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。
• A New Amide, Piperchabamide F, and Two New Phenylpropanoid Glycosides, Piperchabaosides A and B, from the Fruit of Piper chaba
  作者：Toshio Morikawa、Itadaki Yamaguchi、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1248/cpb.57.1292

  日期：——

  A new amide, piperchabamide F (1), and two new phenylpropanoid glycosides, piperchabaosides A (2) and B (3), were isolated from 80% aqueous acetone extract from fruit of Piper chaba. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence.

  从80％的Piper chaba果实丙酮提取液中分离出一种新的酰胺哌沙酰胺F（1）和两个新的苯丙烷糖苷A（2）和B（3）。在化学和物理化学证据的基础上阐明了它们的立体结构。