(3S,4S,5R)-3-amino-4,5-dimethyltetrahydro-2-furanone | 71392-28-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,4S,5R)-3-amino-4,5-dimethyltetrahydro-2-furanone
• 英文别名: (3S,4S,5R)-3-amino-4,5-dimethyloxolan-2-one
• CAS: 71392-28-4
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: DXLUNIWVHZZSPK-WDCZJNDASA-N

物化性质

• 沸点：
  245.6±33.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S,5R)-3-amino-4,5-dimethyltetrahydro-2-furanone 在 lithium hydroxide 、 水 、 溶剂黄146 作用下， 反应 1.0h， 生成 (2S,3S,4R)-γ-hydroxyisoleucine
  参考文献：
  名称：

  Method for preparing diastereoisomers of 4-hydroxy isoleucine

  摘要：

  该发明涉及一种制备4-羟基异亮氨酸的对映异构体的方法，其化学式为CO2H- CH(NH2)- CH(CH3)-CH(OH)-CH3（A），包括以下步骤：去保护胺的B式化合物，还原并随后内酯化C式化合物的中间体胺衍生物，其在2和3位置的取代基为R, S或S, S；或S, R或R, R；水解所得内酯D式化合物，其中在2、3和4位置的取代基为S, R, S或S, R, R，当使用保护胺S, RS, S, S或S, S, R时；当使用保护胺S, SR, S, R或R, S, S时；当使用保护胺R, SR, R, R或R, R, S时；当使用保护胺R, R时，以获得所需的4-羟基异亮氨酸的异构体。用于制备4-羟基异亮氨酸的8种同分异构体的申请。

  公开号：

  EP1657236A1
• 作为产物：
  描述：

  (4S)-4-羟基异亮氨酸 在 盐酸 作用下， 以 水 为溶剂， 反应 6.0h， 生成 (3S,4S,5R)-3-amino-4,5-dimethyltetrahydro-2-furanone
  参考文献：
  名称：

  In vitro anti-hyperglycemic activity of 4-hydroxyisoleucine derivatives

  摘要：

  The nonproteinogenic amino acid, 4-hydroxyisoleucine (1) has been isolated in large quantities from the fenugreek (T. foenurn-graecum) seeds. Few novel derivatives (3-11 and 13-18) were prepared from the naturally occurring 4-hydroxyisoleucine (1) and screened for their in vitro glucose uptake stimulatory effect in L-6 skeletal muscle cells. The derivatives 6, 7, 8, 10 and 11 exhibited better glucose uptake stimulatory activity than parent compound, 4-hydroxyisoleucine at 5 and 10 it M concentrations and compounds 7 and 11 enhanced translocation of insulin sensitive glucose transporters-4 in skeletal muscle cells. (C) 2015 Elsevier GmbH. All rights reserved.

  DOI：

  10.1016/j.phymed.2014.09.007

文献信息

• Compounds and compositions for use in the prevention and treatment of obesity and related syndromes
  申请人：Chapal Nicolas

  公开号：US20060223884A1

  公开（公告）日：2006-10-05

  The invention relates to 4-hydroxyisoleucine, isomers, analogs, lactones, salts, and prodrugs thereof, to processes for their preparation, and to pharmaceutical compositions comprising the same. More particularly, the invention relates to the use of those compounds in the prevention and treatment of obesity and related syndromes.

  本发明涉及4-羟基异亮氨酸、其同分异构体、类似物、内酯、盐和前药，以及它们的制备过程，以及包含它们的药物组合物。更具体地说，本发明涉及这些化合物在预防和治疗肥胖及相关综合症中的用途。
• Syntheses of (−)-Funebrine and (−)-Funebral, Using Sequential Transesterification and Intramolecular Cycloaddition of a Chiral Nitrone
  作者：Osamu Tamura、Nobutaka Iyama、Hiroyuki Ishibashi

  DOI：10.1021/jo030257q

  日期：2004.3.1

  The first syntheses of (−)-funebrine [(−)-1] and (−)-funebral [(−)-2] are described. The syntheses feature sequential formation of nitrone VI from methyl glyoxylate (5) with oxime 6, transesterification of nitrone VI with (E)-crotyl alcohol (4), and intramolecular cycloaddition of the resulting nitrone VII bearing crotyl ester to afford cycloadduct 7 as a major product. The adduct 7 was readily elaborated

  描述了（-）-凤梨碱[（-）- 1 ]和（-）-凤梨碱[（-）- 2 ]的第一合成。合成的特征是由乙醛酸甲酯（5）与肟6依次形成硝酮VI，硝酮VI与（E）-巴豆醇（4）的酯交换反应，以及分子内环加成的含nitr烯基酯的硝酮VII，得到环加成物7，为主要产品。加合物7易于修饰为氨基内酯（-）- 3，这是（-）- 1和（-）- 2的关键合成中间体。
• metabolites. 3. Total synthesis of (±) - funebral, a rotationally restricted pyrrole alkaloid, using a novel Paal-Knorr reaction
  作者：Shao-Xia Yu、Philip W. Le Quesne

  DOI：10.1016/0040-4039(95)01250-l

  日期：1995.8

  The total synthesis of (±) - funebral , a sterically crowded, rotationally restricted pyrrole alkaloid, has been achieved by means of a new variation of the Paal-Knorr synthesis, employing titanium isopropoxide.

  通过使用异丙醇钛的Paal-Knorr合成的新变化，实现了（±）-真菌（一种空间拥挤，受旋转限制的吡咯生物碱）的总合成。
• A Maillard Approach to 2-Formylpyrroles: Synthesis of Magnolamide, Lobechine and Funebral
  作者：Tsz-Ying Yuen、Samantha E. Eaton、Tom M. Woods、Daniel P. Furkert、Ka Wai Choi、Margaret A. Brimble

  DOI：10.1002/ejoc.201301639

  日期：2014.3

  A convenient synthesis of the traditional medicine constituents magnolamide, lobechine and funebral is described. Construction of the 2-formylpyrrole core of these natural products was achieved by means of a Maillard reaction, involving condensation of the sugar surrogate, dihydropyranone 9, with the requisite primary amines. This approach offers a very direct and general route to the 2-formylpyrrole

  描述了传统药物成分木兰酰胺、lobechine 和 funebral 的方便合成。这些天然产物的 2-甲酰基吡咯核心的构建是通过美拉德反应实现的，涉及糖替代物二氢吡喃酮 9 与必需的伯胺的缩合。这种方法为 2-甲酰基吡咯环系统提供了非常直接和通用的途径。
• Total synthesis and absolute structure of N55, a positive modulator of GLP-1 signaling
  作者：Nai-Pin Lin、Rong-Jie Chein

  DOI：10.1039/d0ob01722a

  日期：——

  Glucagon-like peptide-1 (GLP-1) signaling is an established therapeutic target for type 2 diabetes mellitus (T2DM). We developed a 7-step synthesis of N55, a positive modulator of GLP-1 signaling isolated from fenugreek (Trigonella foenum-graecum) seeds, with 29% overall yield, and we determined the absolute structure of N55 to be N-((3R,4R,5S)-4,5-dimethyl-2-oxotetrahydrofur-3-yl)linoleic amide.

  胰高血糖素样肽-1 (GLP-1) 信号传导是 2 型糖尿病 (T2DM) 的既定治疗靶点。我们开发了N55的 7 步合成，这是从葫芦巴 ( Trigonella foenum-graecum ) 种子中分离的 GLP-1 信号的正调节剂，总产率为 29%，我们确定N55的绝对结构为N -((3 R ,4 R ,5 S )-4,5-二甲基-2-氧代四氢呋喃-3-基)亚油酰胺。