β-D-Ribofuranose-1,2,3,5-tetraacetate | 39727-26-9

• 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: β-D-Ribofuranose-1,2,3,5-tetraacetate
• 英文别名: d-Lyxofuranose, tetraacetate；[(2R,3S,4S)-3,4,5-triacetyloxyoxolan-2-yl]methyl acetate
• CAS: 39727-26-9
• 化学式: C₁₃H₁₈O₉
• 分子量: 318.281
• InChiKey: IHNHAHWGVLXCCI-VHGBLZLWSA-N

物化性质

• 沸点：
  125-135 °C(Press: 0.0005 Torr)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  β-D-Ribofuranose-1,2,3,5-tetraacetate 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2R,3S,4S)-2-(acetoxymethyl)-5-bromotetrahydrofuran-3,4-diyl diacetate
  参考文献：
  名称：

  ND-醛糖戊呋喃糖基-N'-[对-（异戊氧基）苯基]-硫脲衍生物：潜在的抗结核治疗药。

  摘要：

  过去，硫代卡利特（THC； N，N'-双[对-（异戊氧基）苯基]-硫脲；也称为异氧基）已被用作抗结核药。为了提高THC的治疗价值，通过苯胺衍生物和戊呋喃糖基异硫氰酸酯的偶联，合成了几种N-戊呋喃糖基-N′-[对-（异戊氧基）苯基]-硫脲衍生物。新产品针对M.tb的MIC值表明，这种合成潜在抗结核病治疗剂的新方法是成功的。

  DOI：

  10.1016/j.bmcl.2008.03.033
• 作为产物：
  描述：

  D-lyxose 在 吡啶 、 Dowex 8x50W 、 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 11.5h， 生成 β-D-Ribofuranose-1,2,3,5-tetraacetate
  参考文献：
  名称：

  大肠杆菌的核苷转运蛋白NupC和NupG：配体结合所必需的特定结构基序。

  摘要：

  测试了一系列46种天然核苷和类似物（主要是基于腺苷的）作为从大肠杆菌中富集的，与H（+）连接的核苷转运蛋白NupC和NupG吸收[U-（14）C]尿苷的抑制剂。这两个在进化上不相关的转运蛋白显示出相似但不同的抑制模式，揭示了对不同核苷及其类似物的不同选择性。核苷与NupG的结合需要在核糖的C-3'和C-5'位置分别存在羟基，而与NupC的结合仅需要C-3'羟基取代基。核糖部分对于结合NupG的重要性更高，与该蛋白质和寡糖之间的进化关系一致：运输者的主要促进者超家族（MFS）的H（+）同向转运蛋白（OHS）亚家族。对于两种蛋白质，C-3'处的天然α-构型和C-1'处的天然β-构型对于配体结合都是必需的。发现腺苷的咪唑环中的N-7和C-6的氨基对于结合并不重要，并且两个转运蛋白都显示出C-6 / N取代的灵活性。N-1和N-3中的一个或两个对腺苷类似物与NupC的结合很重要，但对NupG的结合

  DOI：

  10.1039/b414739a

文献信息

• Synthesis of modified D-mannose core derivatives and their impact on GH38 α-mannosidases
  作者：Monika Poláková、Radim Horák、Sergej Šesták、Ivana Holková

  DOI：10.1016/j.carres.2016.04.004

  日期：2016.6

  Nine new compounds having five- and modified six-member carbohydrate core derived from D-lyxose or D-mannose, and non-hydrolysable aglycones (benzylsulfonyl or aryl(alkyl)triazolyl) were synthesised to investigate their ability to inhibit the recombinant Drosophila melanogaster homologs of two human GH38 family enzymes: Golgi mannosidase II (dGMIIb) and lysosomal mannosidase (dLMII). Two compounds

  合成了九种新化合物，这些化合物具有衍生自D-lyxose或D-甘露糖的五元和六元碳水化合物核心，以及不可水解的糖苷配基（苄基磺酰基或芳基（烷基）三唑基），以研究其抑制重组果蝇果蝇同系物的能力。两种人类GH38家族酶中的一种：高尔基甘露糖苷酶II（dGMIIb）和溶酶体甘露糖苷酶（dLMII）。两种化合物是弱选择性dGMIIb抑制剂，在mM水平下显示IC50。此外，发现另一种GH38酶，商品菜豆α-甘露糖苷酶，无论碳水化合物核心如何，都被三唑缀合物抑制，而相应的砜是无活性的。
• Synthesis and antiviral activity of certain guanosine analogs in the thiazolo[4,5-d]pyrimidine ring system
  作者：Ganesh D. Kini、Jack D. Anderson、Yogesh S. Sanghvi、Arthur F. Lewis、Donald F. Smee、Ganapathi R. Revankar、Roland K. Robins、Howard B. Cottam

  DOI：10.1021/jm00114a008

  日期：1991.10

  Several sugar-modified nucleoside derivatives of the purine analogue 5-amino-3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidine-2,7-dione (1) were synthesized. Phosphorylation of 1 using POCl3 resulted in 5'-monophosphate 2, which was subsequently converted to 3',5'-cyclic phosphate 3, by reported methods. 5'-Sulfamoyl derivative 4 was synthesized by treatment of the 2,3-O-isopropylidene derivative of

  合成了嘌呤类似物5-氨基-3-β-D-呋喃核糖基噻唑并[4,5-d]嘧啶-2,7-二酮（1）的几种糖修饰的核苷衍生物。使用POCl3进行1的磷酸化反应，生成5'-单磷酸2，随后通过报道的方法转化为3'，5'-环磷酸3。通过用氯磺酰胺处理1的2，3-O-异亚丙基衍生物，然后进行酸脱保护，来合成5'-氨磺酰基衍生物4。化合物5-7、1的5'-脱氧，三-O-乙酰基和2'-脱氧衍生物分别通过5-氨基噻唑并[4,5-d]嘧啶-2,7的糖基化反应合成-二酮，1的糖苷配基，具有适当的糖部分，采用Vorbruggen程序。C2'-C3'的氧化裂解 在1中结合键，然后用硼氢化钠还原产生“ seco”类似物8。评价了核苷2-8在体内对Semliki森林病毒的抗病毒活性。化合物2、5和7的活性类似于1的活性。环状磷酸酯3在高剂量时有毒，而在低剂量时则弱。化合物4、6和8在该系统中没有活性。
• Conversion of Pyranose Glycals to Furanose Derivatives:  A New Route to Oligofuranosides
  作者：Francis W. D'Souza、Pavel E. Cheshev、Joseph D. Ayers、Todd L. Lowary

  DOI：10.1021/jo9815406

  日期：1998.11.1

  Acetylated pyranose glycals have been converted through a convenient three-step process into protected furanose reducing sugars. Ozonolysis of 2,3,5-tri-O-acetyl-glucal or 2,3,5-tri-O-acetyl-galactal, followed by treatment with dimethyl sulfide and then hydrolysis gave respectively protected arabinofuranose (6) and lyxofuranose (7) derivatives. Conversion of these hemiacetals to oligosaccharides was explored using a number of methods. Activation of 6 or 7 in situ afforded glycosides in modest yield and stereoselectivity. Glycosylation of tetraacetates 16 and 18, obtained from 6 and 7, gave similar results. However, thioglycosides 17 and 19, also derived from 6 and 7, were found to be effective glycosyl donors, producing products in good to excellent yields and with high stereoselectivities. The method was also used to synthesize a disaccharide in which one residue contained uniform C-13 enrichment.
• Simple and efficient per-O-acetylation of carbohydrates by lithium perchlorate catalyst
  作者：Kuo-Cheng Lu、Shu-Yi Hsieh、Laxmikant N. Patkar、Chien-Tien Chen、Chun-Cheng Lin

  DOI：10.1016/j.tet.2004.06.138

  日期：2004.9

  Lithium perchlorate is demonstrated to be a highly efficient and convenient catalyst for the per-O-acetylation of various saccharides with excellent yields. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.