L-来苏糖酸-1,4-内酯 | 104196-15-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: L-来苏糖酸-1,4-内酯
• 英文名称: lyxonic acid-1,4-lactone
• 英文别名: L-lyxono-1,4-lactone；L-lyxonolactone；L-lyxono-γ-lactone；(3R,4S,5S)-3,4-Dihydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one；(3R,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one
• CAS: 104196-15-8
• 化学式: C₅H₈O₅
• 分子量: 148.116
• InChiKey: CUOKHACJLGPRHD-PZGQECOJSA-N

物化性质

• 沸点：
  364.3±11.0 °C(Predicted)
• 密度：
  1.667±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  10
• 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：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-来苏糖酸-1,4-内酯 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 锂硼氢 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 2,3-bis-O-tert-butyldimethylsilyl-1,4-bis-O-methanesulfonyl-5-O-triphenylmethyl-L-lyxitol
  参考文献：
  名称：

  Toward a General Strategy for the Synthesis of 3,4-Dihydroxyprolines from Pentose Sugars

  摘要：

  A general strategy is proposed, wherein a pentose sugar gamma-lactone can be converted, via a series of nine reactions, to a 3,4-dihydroxyproline, suitably protected for use in peptide synthesis. Thus, D-ribonolactone (6) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-D-2,3-cis-3,4-cis-proline (7) in 18.9% overall yield. Likewise, L-arabinonolactone (11) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-L-2,3-cis-3,4-trans-proline (36) in 13.7% overall yield and L-lyxonolactone (12) to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-L-2,3-trans-3,4-cis-proline (37) in 11.2% overall yield. These building blocks have also been fully deprotected to give the free amino acids. We believe that this series of reactions ought to be applicable to the synthesis of any of the eight stereoisomers of 3,4-dihydroxyproline, by judicious selection of the pentose starting material.

  DOI：

  10.1021/jo025538x
• 作为产物：
  描述：

  L-来苏糖 在 次碘(I)酸 作用下， 生成 L-来苏糖酸-1,4-内酯
  参考文献：
  名称：

  Supramolecular Assemblies of Diacetylenic Aldonamides

  摘要：

  The study of novel amphiphiles that form nonspheroidal assemblies upon hydration is fundamental to understanding the relationship between molecular structure and supramolecular morphology. Structural components of previously reported amphiphiles were used to design the single chain diacetylenic aldonamides reported here. Open chain sugar headgroups were linked via an amide bond to a hydrophobic tail. Diacetylenes were incorporated in the alkyl chain both as a structural component and as a reactive unit. Photopolymerization was used to test the molecular ordering of the hydrophobic region of the assemblies and to enhance their thermal and chemical stability. The electron density of the diacetylenes allowed direct imaging of the assemblies by TEM. The morphology and reactivity of a series of N-dodeca-5,7-diynylaldonamides were determined. The aldonamides were derived from two aldoheptoses, D-glycero-D-gluconamide and D-glycero-L-mannonamide; four aldohexoses, D-galactonamide, D-gluconamide, L-mannonamide, and D-gulonomide; two aldopentoses, L-arbanonamide and L-lyxonamide; and two aldotetroses, L-threonamide and D-erythronamide. N-Dodecylaldonamide analogues were prepared and examined to evaluate the importance of the diacetylene group on the morphology. The microscopy and molecular modeling data indicate that at least two packing arrangements for these assemblies are possible. One is the head-to-head bilayer packing typical of most amphiphilic molecules; the other is a head-to-tail arrangement. The head-to-head packing results in assemblies which are planar, helical, or tubular. The head-to-tail packing arrangement and ''dromic'' hydrogen-bonding patterns are associated with fiber-like supramolecular assemblies. Numerous potential applications of tubule microstructures have been proposed. The relative ease of preparation of many of these aldonamide molecules and their assemblies recommends them for many of these applications.

  DOI：

  10.1021/ja00101a026

文献信息

• Maillard Degradation Pathways of Vitamin C
  作者：Mareen Smuda、Marcus A. Glomb

  DOI：10.1002/anie.201300399

  日期：2013.4.26

  Degradation mechanisms: 75 % of the Maillard degradation pathways of ascorbic acid can be explained by oxidative α fragmentation (31 %), β cleavage (32 %), and decarboxylation from hydrate/hemiaminal intermediates (12 %), which lead to carbonyl and dicarbonyl compounds, carboxylic acids, and amide advanced glycation endproducts. The results are a major step forward in the understanding of changes occurring

  降解机理：抗坏血酸美拉德降解途径的75％可以通过氧化性α片段化（31％），β裂解（32％）和水合物/半缩醛中间体的脱羧作用（12％）来解释，这导致羰基和二羰基化合物，羧酸和酰胺高级糖基化终产物。该结果是在理解含维生素C的系统中发生的变化方面迈出的重要一步。
• A New Efficient Access to Glycono-1,4-lactones by Oxidation of Unprotected Itols by Catalytic Hydrogen Transfer with RhH(PPh₃)₄-Benzalacetone System
  作者：I. Isaac、G. Aizel、I. Stasik、A. Wadouachi、D. Beaupère

  DOI：10.1055/s-1998-1705

  日期：1998.5

  Treatment of unprotected pentitols and hexitols with RhH(PPh3)4-benzalacetone system leads exclusively to glycono-1,4-lactones in 60-96% yield.

  使用RhH(PPh3)4-苯甲醛乙酮体系处理未保护的戊糖醇和己糖醇，可专一性地以60-96%的产率生成糖醛-1,4-内酯。
• PYRROLIDINE DERIVATIVES AS SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF
  申请人：Summit Corporation Plc

  公开号：US20140073801A1

  公开（公告）日：2014-03-13

  Disclosed are compounds of formula (I): or a pharmaceutically acceptable salt, derivative, solvate, isomer, tautomer, N-oxide, ester, prodrug, isotope or protected form thereof, which are of use as OGA inhibitors, for example in the treatment of various conditions and diseases, including neurodegenerative disorders.

  公开了以下式（I）的化合物：或其药用盐、衍生物、溶剂合物、异构体、互变异构体、N-氧化物、酯、前药、同位素或其保护形式，这些化合物可用作OGA抑制剂，例如在治疗各种疾病和疾病，包括神经退行性疾病方面。
• A Facile and General Synthesis of Rare <scp>l</scp>-Sugar Lactones
  作者：Rawle Hollingsworth、Xuezheng Song

  DOI：10.1055/s-2007-977451

  日期：——

  A facile and general synthesis of rare L-sugar lactones from D-sugars by selectively inverting C-5 was developed. Selective 1-deacylation of sugar perpivaloates by hydroxylamine is described. More practically, β- D-glucose pentaacetate could be transformed to L- IDONO-1,4-lactones by this simple procedure.

  开发了一种通过选择性反转 C-5 从 D-糖中合成稀有 L-糖内酯的简便方法。描述了羟胺对糖过新戊酸酯的选择性 1-脱酰。更实际的是，β-D-葡萄糖五乙酸酯可以通过这个简单的程序转化为 L-IDONO-1,4-内酯。
• [EN] PYRROLIDINE DERIVATIVES AS SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF<br/>[FR] DÉRIVÉS DE PYRROLIDINE EN TANT QU'INHIBITEURS SÉLECTIFS DE GLYCOSIDASE ET LEURS UTILISATIONS
  申请人：SUMMIT CORP PLC

  公开号：WO2012117219A1

  公开（公告）日：2012-09-07

  Disclosed are compounds of formula (I) or a pharmaceutically acceptable salt, derivative, solvate, isomer, tautomer, N-oxide, ester, prodrug, isotope or protected form thereof, which are of use as OGA inhibitors, for example in the treatment of various conditions and diseases, including neurodegenerative disorders.

  揭示了式(I)的化合物或其药用可接受的盐、衍生物、溶剂合物、异构体、互变异构体、N-氧化物、酯、前药、同位素或其保护形式，可用作OGA抑制剂，例如用于治疗各种疾病和症状，包括神经退行性疾病。