L-lyxofuranose | 532-20-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-lyxofuranose
• 英文别名: L-lyxose；L-lyxose；(3R,4S,5S)-5-(hydroxymethyl)oxolane-2,3,4-triol
• CAS: 532-20-7；613-83-2；7261-25-8；7687-39-0；13221-22-2；14795-83-6；15761-67-8；20074-49-1；25545-03-3；25545-04-4；32445-75-3；36441-93-7；36468-53-8；37110-85-3；37388-49-1；38029-69-5；40461-77-6；40461-89-0；41546-19-4；41546-20-7；41546-21-8；41546-26-3；41546-29-6；41546-30-9；41546-31-0；126872-16-0；131064-98-7；34436-17-4
• 化学式: C₅H₁₀O₅
• 分子量: 150.131
• InChiKey: HMFHBZSHGGEWLO-AEQNFAKKSA-N

物化性质

• 沸点：
  375.4±42.0 °C(Predicted)
• 密度：
  1.681±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

制备方法与用途

D-核糖（D-Ribose）是一种存在于脑脊液中的内源性代谢产物，可用于研究核糖5-磷酸异构酶缺乏症和中链酰基辅酶A脱氢酶缺乏症。

反应信息

• 作为反应物：
  描述：

  L-lyxofuranose 在 吡啶 、 咪唑 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 氨 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 1-{5-O-t-butyldiphenylsilyl-2,3-di-O-[methylthio(thiocarbonyl)]-α-L-lyxofuranosyl}-5-fluorocytosine
  参考文献：
  名称：

  Total Synthesis of α-Elvucitabine

  摘要：

  Total synthesis of alpha-elvucitabine was achieved in 26% overall yield by a concise nine-step procedure starting from L-lyxose, with trimethylsilyl trifluoromethaneoulfonate (TMSOTf)-mediated stereocontrolled alpha-N-glycosidation and olefination through Barton-McCombie deoxygenation being the key steps, and the stereochemistry of the product was determined by nuclear Overhauser effect spectroscopy.

  DOI：

  10.1080/00397911.2011.571805
• 作为产物：
  描述：

  L-lyxose 在 硫酸 、 copper(II) sulfate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 L-lyxofuranose
  参考文献：
  名称：

  Adenosine Kinase Inhibitors. 3. Synthesis, SAR, and Antiinflammatory Activity of a Series of l-Lyxofuranosyl Nucleosides

  摘要：

  Chronic inflammatory diseases, such as arthritis and rheumatoid arthritis, remain major health problems worldwide. We previously demonstrated that adenosine kinase inhibitors (AKIs) exhibit antiinflammatory effects by inhibiting TNF-alpha production, neutrophil accumulation, and edema formation. Although adenosine receptor agonists produce similar effects, AKIs showed the antiinflammatory activity without the cardiovascular side effects that prevented the development of adenosine receptor specific agonists. However, previously described potent AKIs, such as 5-iodotubercidin, are nucleosides which have the potential to undergo in vivo 5'-O-phosphorylation and therefore produce cytotoxicity. In an effort to eliminate toxicities produced by phosphorylated nucleosides, L-lyxofuranosyl analogues of tubercidin were tested as potential AKIs since the opposite stereochemical. orientation of the CH2OH was expected to eliminate intracellular phosphorylation. Described herein are the discovery of a new series of AKIs based on alpha-L-lyxofuranosyl. nucleosides, their SAR, as well as the antiinflammatory activity of the lead compound GP790 (IC50 = 0.47 nM, 47% inhibition of paw swelling at 10 mg/kg in rat carrageenan paw edema model). In addition, a study showing that in the skin lesion model the antiinflammatory activity is reversed by an A2 selective adenosine receptor antagonist 3,7-dimethyl-1-propylxanthine (DMPX) is also described.

  DOI：

  10.1021/jm030230z

文献信息

• A Novel Pentose Synthesis via Palladium(II)-Catalyzed Cyclization of an Unstable Hemiacetal
  作者：Masahiro Miyazawa、Yoshiro Hirai、Ken-ichiro Awasaguchi、Koichi Inoue、Koji Nakamura、Hajime Yokoyama、Ikuyo Uoya

  DOI：10.3987/com-10-12001

  日期：——

  -hexenal and methanol gave substituted furanoside in moderate yield, exclusively via 5-exo-mode cyclization, without the need for a reoxidant. New stereogenic centers at C1 and C4 on the tetrahydrofuran ring showed preferential 1R and 4R stereochemistry due to anomeric effect (n o -σ * c-o ) and A 1,2 strain, respectively. This methodology was applied to stereocontrolled synthesis of pentoses: D-ribose

  PdCl 2 (PhCN) 2 (5 mol%)-催化由 (E,2S,3R)-2,3-异亚丙基二氧基-6-(四氢-2H-吡喃-2-基)-4-己烯醛衍生的半缩醛环化甲醇以中等收率产生取代的呋喃糖苷，仅通过 5-外模式环化，无需再氧化剂。由于异头效应（无 -σ * co ）和 A 1,2 应变，四氢呋喃环上 C1 和 C4 处的新立体中心分别显示出优先的 1R 和 4R 立体化学。该方法应用于戊糖的立体控制合成：D-核糖和 L-来苏糖。
• Design, Synthesis, and Antiviral Activity of α-Nucleosides:  <scp>d</scp>- and <scp>l</scp>-Isomers of Lyxofuranosyl- and (5-Deoxylyxofuranosyl)benzimidazoles
  作者：Michael T. Migawa、Jean-Luc Girardet、John A. Walker、George W. Koszalka、Stanley D. Chamberlain、John C. Drach、Leroy B. Townsend

  DOI：10.1021/jm970545c

  日期：1998.4.1

  Several 2-substituted alpha-D- and alpha-L-lyxofuranosyl and 5-deoxylyxofuranosyl derivatives of 5,6-dichloro-2-(isopropylamino)-1- -(beta-L-ribofuranosyl)benzimidazole (1263W94) and 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB) were synthesized and evaluated for activity against two herpesviruses (HSV-1 and HCMV) and for their cytotoxicity against HFF and KB cells. Condensation of 1,2,3,5-tetra-O-acetyl-L-lyxofuranose (2a) with 2,5,6-trichlorobenzimidazole (1) yielded the or-nucleoside 3a. The 2-bromo derivative and 2-methylamino derivative were prepared by treatment of 3a with HBr followed by deprotection or from methylamine, respectively. Compound 3a was deprotected and the resultant nucleoside used to prepare the 2-cyclopropylamino and 2-isopropylamino derivatives. The 2-alkylthio nucleosides were prepared by condensing 2a with 5,6-dichlorobenzimidazole-2-thione followed by deprotection. Alkylation of this adduct gave the 2-methylthio and 2-benzylthio derivatives. Condensation of 5-deoxy-1,2,3-tri-O-acetyl-L-lyxofuranosyl, prepared from L-lyxose, with 1 or 2-bromo-5,6-dichlorobenzimidazole (15), followed by deprotection, gave the 2-chloro or 2-bromo-5'-deoxylyxofuranosyl derivative, respectively. The cyclopropylamino derivative was prepared from the 2-chloro derivative. All D-isomers were prepared in an analogous fashion from D-lyxose. Either compounds were inactive against HSV-1 or weak activity was poorly separated from cytoxicity. In contrast, the 2-halogen derivatives in both the alpha-lyxose and 5-deoxy-alpha-lyxose series were active against the Towne strain of HCMV. The 5-deoxy alpha-L analogues were the most active, IC50's = 0.2-0.4 mu M, plaque assay; IC90's = 0.2-2 mu M, yield reduction assay. All of the 2-isopropylamino or 2-cyclopropylamino derivatives were less active (IC50's = 60-100 mu M, plaque assay; IC90's = 17-100 mu M, yield reduction assay) and were not cytotoxic. The methylamino, thio, and methylthio derivatives were neither active nor cytotoxic. The benzylthio derivatives were weakly active, but this activity was poorly separated from cytotoxicity. The alpha-lyxose L-isomers were more active in a plaque assay against the AD169 strain of HCMV compared to the Towne strain, thereby providing additional evidence of antiviral specificity.
• Total Synthesis of α-Elvucitabine
  作者：Guilong Zhao、Yuanyuan Lou、Linshan Zhang、Hua Shao、Weiren Xu、Lida Tang、Meixiang Zou

  DOI：10.1080/00397911.2011.571805

  日期：2012.10

  Total synthesis of alpha-elvucitabine was achieved in 26% overall yield by a concise nine-step procedure starting from L-lyxose, with trimethylsilyl trifluoromethaneoulfonate (TMSOTf)-mediated stereocontrolled alpha-N-glycosidation and olefination through Barton-McCombie deoxygenation being the key steps, and the stereochemistry of the product was determined by nuclear Overhauser effect spectroscopy.
• Adenosine Kinase Inhibitors. 3. Synthesis, SAR, and Antiinflammatory Activity of a Series of <scp>l</scp>-Lyxofuranosyl Nucleosides
  作者：Bheemarao G. Ugarkar、Angelo J. Castellino、Jay S. DaRe、Michele Ramirez-Weinhouse、Joseph J. Kopcho、Sanna Rosengren、Mark D. Erion

  DOI：10.1021/jm030230z

  日期：2003.10.1

  Chronic inflammatory diseases, such as arthritis and rheumatoid arthritis, remain major health problems worldwide. We previously demonstrated that adenosine kinase inhibitors (AKIs) exhibit antiinflammatory effects by inhibiting TNF-alpha production, neutrophil accumulation, and edema formation. Although adenosine receptor agonists produce similar effects, AKIs showed the antiinflammatory activity without the cardiovascular side effects that prevented the development of adenosine receptor specific agonists. However, previously described potent AKIs, such as 5-iodotubercidin, are nucleosides which have the potential to undergo in vivo 5'-O-phosphorylation and therefore produce cytotoxicity. In an effort to eliminate toxicities produced by phosphorylated nucleosides, L-lyxofuranosyl analogues of tubercidin were tested as potential AKIs since the opposite stereochemical. orientation of the CH2OH was expected to eliminate intracellular phosphorylation. Described herein are the discovery of a new series of AKIs based on alpha-L-lyxofuranosyl. nucleosides, their SAR, as well as the antiinflammatory activity of the lead compound GP790 (IC50 = 0.47 nM, 47% inhibition of paw swelling at 10 mg/kg in rat carrageenan paw edema model). In addition, a study showing that in the skin lesion model the antiinflammatory activity is reversed by an A2 selective adenosine receptor antagonist 3,7-dimethyl-1-propylxanthine (DMPX) is also described.