(3R,4S,5S)-3,4-dihydroxy-5-methyl-dihydro-furan-2-one | 248256-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,4S,5S)-3,4-dihydroxy-5-methyl-dihydro-furan-2-one
• 英文别名: (3R,4S,5S)-3,4-dihydroxy-5-methyloxolan-2-one
• CAS: 248256-29-3
• 化学式: C₅H₈O₄
• 分子量: 132.116
• InChiKey: JYHWQRJRDKSSIF-PZGQECOJSA-N

物化性质

• 沸点：
  263.9±7.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (3R,4S,5S)-3,4-dihydroxy-5-methyl-dihydro-furan-2-one 在 吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 (4RS,5RS)-4-hydroxy-5-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  由手可得的碳水化合物作为手性模板，首次不对称合成马来酸内酯

  摘要：

  通过使用肉豆蔻醛与β-羟基内酯烯醇烯酸酯的二价阴离子的立体选择性烷基化，实现了简单有效的首次合成马里酰内酯的不对称策略。关键中间体β-羟基γ-甲基丁内酯是通过从D-核糖（一种天然丰富的手性碳水化合物）开始转化L-羟内酯来制备的。

  DOI：

  10.1016/j.carres.2016.06.005
• 作为产物：
  描述：

  L(-)岩藻糖 在 氢氧化钾 作用下， 生成 (3R,4S,5S)-3,4-dihydroxy-5-methyl-dihydro-furan-2-one
  参考文献：
  名称：

  Clark, Journal of Biological Chemistry, 1922, vol. 54, p. 65,69

  摘要：

  DOI：

文献信息

• Stoffwechselprodukte von Mikroorganismen. 202. Mitteilung. Strukturaufklärung von Elaiophylin: Spektroskopische Untersuchungen und Abbau
  作者：Hanspeter Kaiser、Walter Keller-Schierlein

  DOI：10.1002/hlca.19810640206

  日期：1981.3.18

  Structure Elucidation of Elaiophylin: Spectroscopy and Chemical Degradation

  Elaiophylin的结构阐明：光谱学和化学降解
• Studies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides
  作者：Steven V. Ley、Darren J. Dixon、Richard T. Guy、Maria A. Palomero、Alessandra Polara、Félix Rodríguez、Tom D. Sheppard

  DOI：10.1039/b412790k

  日期：——

  Highly diastereoselective coupling reactions of enolates derived from butane-2,3-diacetal protected glycolic acids 1 and 2 and their alkylated derivatives with aldehydes are reported together with their efficient acid-catalysed deprotection to yield enantiopure anti-2,3-dihydroxyesters. A procedure to provide the corresponding syn-2,3-dihydroxyesters is also described in two cases, proceeding via an acylation–reduction sequence. An usual double addition reaction of butane-2,3-diacetal protected glycolic acid to small aliphatic acid chlorides provides a synthetically useful, densely-functionalised lactone after acidic deprotection.

  报告了来自丁烷-2,3-二缩醛保护的羟基酸1和2及其烷基化衍生物与醛的高立体选择性偶联反应，并且有效的酸催化去保护反应能够生成对映体纯的反-2,3-二羟基酯。同时，在两种情况下也描述了一种提供相应顺-2,3-二羟基酯的程序，该程序通过酰化-还原序列进行。丁烷-2,3-二缩醛保护的羟基酸与小型脂肪酸氯化物的常规双重加成反应在酸去保护后提供了一种合成上有用的、密集功能化的内酯。
• 말리올라이드 유도체를 유효성분으로 함유하는 항산화용 조성물
  申请人：TAENAM MEDICOS CO.,LTD 태남메디코스 주식회사(120150309951) Corp. No ▼ 154511-0061608BRN ▼303-81-77538

  公开号：KR102007282B1

  公开（公告）日：2019-08-06

  본 발명은 말리올라이드 유도체 및 이를 유효성분으로 함유하는 항산화용 조성물에 관한 것으로, 상기 말리올라이드 유도체는 세포독성 없이 항산화관련 단백질의 발현을 조절하는 전사인자 Nrf2의 발현을 증가시킴으로써, 항산화 관련 단백질인 HO-1 및 NQO1의 발현을 증가시켰으며, 산화적 스트레스를 유발시키는 TPA에 의해 유도된 DNA 및 지질의 산화를 억제하는 것으로 확인됨에 따라, 상기 말리올라이드 유도체를 유효성분으로 함유하는 조성물은 항산화용 조성물로 제공될 수 있다.

  本发明涉及马里奥酰胺衍生物及其作为有效成分含有抗氧化剂的组合物，所述马里奥酰胺衍生物通过增加转录因子Nrf2的表达来调节抗氧化相关蛋白的表达，而无细胞毒性，增加了抗氧化相关蛋白HO-1和NQO1的表达，并且通过抑制由TPA诱导的DNA和脂质氧化，确认其抑制氧化应激。因此，含有上述马里奥酰胺衍生物作为有效成分的组合物可作为抗氧化剂组合物提供。
• Highly Diastereoselective Lithium Enolate Aldol Reactions of Butane-2,3-diacetal Desymmetrized Glycolic Acid and Deprotection to Enantiopure <i>anti</i>-2,3-Dihydroxy Esters
  作者：Darren J. Dixon、Steven V. Ley、Alessandra Polara、Tom Sheppard

  DOI：10.1021/ol016707n

  日期：2001.11.1

  [reaction--see text] The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block 1 undergoes efficient and highly diastereoselective lithium enolate aldol reactions with both aromatic and aliphatic aldehydes to afford, after an acidic methanolysis deprotection step, the enantiopure anti-2,3-dihydroxy esters in good yield.

  [反应-参见文本]异丁烷2,3-二缩醛（BDA）乙醇酸结构单元1与芳香族和脂肪族醛进行高效且高度非对映选择性的烯醇酸锂醛醇缩醛反应，从而在酸性甲醇分解脱保护步骤后得到对映体纯的抗2,3-二羟基酯，收率良好。
• A convenient preparation of aldonohydroxamic acids in water and crystal structure of l-erythronohydroxamic acid
  作者：Laurent Salmon、Elise Prost、Claude Merienne、Renaud Hardré、Georges Morgant

  DOI：10.1016/s0008-6215(01)00210-5

  日期：2001.10

  Hydroxamic acids derived from aldonic acids, namely aldonohydroxamic acids, have become an increasingly important class of inhibitors of enzymes involved in the metabolism of carbohydrates. We now report the straightforward preparation of various types of aldonohydroxamic acids by a new methodology involving the use of commercial 50% aqueous hydroxylamine as the source of the free base hydroxylamine that reacts directly with the corresponding aldonolactone dissolved in water. The reaction proceeds almost instantaneously in water at room temperature, yielding generally pure products in quantitative yield. To date, this methodology is probably the most facile and efficient way to synthesize aldonohydroxamic acids. We also determined by X-ray diffraction analysis the first crystal structure of a free aldonohydroxamic acid reported to date. Crystals of L-erythronohydroxamic acid belonged to the monoclinic system, space group P2(1), a = 5.511(3), b = 7.556(1), c = 8.071(3) Angstrom, beta = 109.10 degrees, and Z = 2. (C) 2001 Elsevier Science Ltd. All rights reserved.