1-(1'-deoxy-2',3',4'-tri-O-acetyl-β-D-xylopyranos-1'-yl)propan-2-one | 439685-75-3

• 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: 1-(1'-deoxy-2',3',4'-tri-O-acetyl-β-D-xylopyranos-1'-yl)propan-2-one
• 英文别名: 1-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyl)-propan-2-one；1-(2,3,4,-tri-O-acetyl-β-D-xylopyranosyl)propan-2-one；1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-propan-2-one；1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)propane-2-one；1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)propan-2-one；2,3,4-tri-O-acetyl-β-D-xylopyranosylpropane-2-one；[(3R,4S,5S,6S)-4,5-diacetyloxy-6-(2-oxopropyl)oxan-3-yl] acetate
• CAS: 439685-75-3
• 化学式: C₁₄H₂₀O₈
• 分子量: 316.308
• InChiKey: AXJFUNASXQEMPD-CRWXNKLISA-N

物化性质

• 沸点：
  382.5±35.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(1'-deoxy-2',3',4'-tri-O-acetyl-β-D-xylopyranos-1'-yl)propan-2-one 在 四氢吡咯 、 tin(II) chloride dihdyrate 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 (E)-4-[3-(3-phenylureido)phenyl]-1-[1′-deoxy-β-D-xylopyranos-1′-yl]but-3-en-2-one
  参考文献：
  名称：

  Identification of Novel Phenyl Butenonyl C-Glycosides with Ureidyl and Sulfonamidyl Moieties as Antimalarial Agents

  摘要：

  A new series of C-linked phenyl butenonyl glycosides bearing ureidyl(thioureidyl) and sulfonamidyl moieties in the phenyl rings were designed, synthesized, and evaluated for their in vitro antimalarial activities against Plasmodium falciparum 3D7 (CQ sensitive) and K1 (CQ resistant) strains. Among all the compounds screened the C-linked phenyl butenonyl glycosides bearing sulfonamidyl moiety (5a) and ureidyl moiety in the phenyl ring (7d and 8c) showed promising antimalarial activities against both 3D7 and K1 strains with IC50 values in micromolar range and low cytotoxicity offering new HITS for further exploration.

  DOI：

  10.1021/ml500211c
• 作为产物：
  描述：

  D-木糖 在 吡啶 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 1-(1'-deoxy-2',3',4'-tri-O-acetyl-β-D-xylopyranos-1'-yl)propan-2-one
  参考文献：
  名称：

  CN116574080

  摘要：

  公开号：

文献信息

• A novel class of sugar-based ether-linked-dispirooxindolo-pyrrolidines/pyrrolizidines through [3+2]-cycloaddition of azomethine ylides
  作者：Arasappan Hemamalini、Subbiah Nagarajan、Thangamuthu Mohan Das

  DOI：10.1016/j.carres.2012.01.023

  日期：2012.5

  An efficient one-pot synthesis of novel sugar based dispirooxindolo-pyrrolidines/pyrrolizidines has been accomplished by a [3+2]-cycloaddition. This method utilizes an azomethine ylide derived from isatin and sarcosine/l-proline, with an ether linked alpha-,beta-unsaturated-beta-C-glycosidic ketones as the dipolarophile. All these sugar-based heterocyclics were characterized by NMR ((1)H and (13)C)

  通过[3 + 2]-环加成反应，可以有效地一锅合成新型的基于糖的双螺毒素-吡咯烷/吡咯烷。该方法利用了衍生自靛红和肌氨酸/ 1-脯氨酸的偶氮甲碱叶立德，以及与醚连接的α-，β-不饱和β-C-糖苷酮作为双极性亲和剂。所有这些基于糖的杂环都通过NMR（（1）H和（13）C）和元素分析进行​​了表征。糖基双螺杂环化合物10的抗微生物研究显示了对不同微生物的出色活性。
• Studies on the synthesis of ether-, substituted alkyl-, or aryl-linked C-disaccharide derivatives
  作者：Subbiah Nagarajan、M. Jeganathan Shanmugam、Thangamuthu Mohan Das

  DOI：10.1016/j.carres.2011.02.009

  日期：2011.5

  A series of ether-, substituted alkyl-, or aryl-linked disaccharide derivatives have been synthesized in relatively good yield and characterized using different spectral techniques including single-crystal X-ray diffraction (XRD). β-Anomeric forms of sugar moiety in these derivatives were identified from (1)H NMR studies. The existence of inter- and intramolecular hydrogen bonding interactions were

  已经以相对较高的产率合成了一系列醚，取代的烷基或芳基连接的二糖衍生物，并使用包括单晶X射线衍射（XRD）在内的不同光谱技术对其进行了表征。这些衍生物中糖部分的β-端基异构形式是通过（1）H NMR研究确定的。从单晶XRD研究确定了分子间和分子内氢键相互作用的存在。
• Exploration, synthesis and studies of gel forming simple sugar-chalcone derivatives
  作者：Arasappan Hemamalini、Thangamuthu Mohan Das

  DOI：10.1039/c4ra06544a

  日期：——

  Simple sugar-chalcone derivatives have been obtained by aldol condensation where aglycon–chalcone dimer was obtained as an unexpected product in addition to the sugar-chalcone

  简单糖-香豆素衍生物通过醛缩合成得，其中除了糖-香豆素外，还意外得到了缺苷-香豆素二聚体。
• Facile One-Pot Synthesis of Inden-1-ol Derivatives
  作者：Thangamuthu Das、Subbiah Nagarajan、Paneerselvam Muthuvel

  DOI：10.1055/s-0030-1261196

  日期：2011.9

  Abstract: A facile one-pot synthesis of a novel class of inden-1-ol/indanone derivatives has been developed and formation of ionicclusters by lithium perchlorate has been demonstrated using UV-visstudies. Key words: methyl ketones, o -phthaldialdehyde, inden-1-ol deriv-atives, b-anomer, XRD analysis Carbon–carbon bond formation remains an importantchallenge for synthetic organic chemists. 1,2 Among

  摘要：已经开发了一种新型茚-1-醇/茚满酮衍生物的简便一锅法合成方法，并已使用紫外可见研究证明了高氯酸锂形成离子簇的方法。关键词：甲基酮，邻苯二甲醛，inden-1-ol 衍生物，b-端基异构体，XRD 分析碳-碳键的形成仍然是合成有机化学家面临的一个重要挑战。1,2 在不同的 C-C 键形成反应中，Morita-Baylis-Hillman 反应 (MBH) 3-5 自 1990 年代中期以来受到越来越多的关注，因为它在催化剂的存在下转化简单的起始材料，例如作为三烷基膦，6哌可酸，N-甲基咪唑，7或三苯基膦8成高度官能化的化合物，可用于进一步转化。4 此外，分子内 BH 闭环反应为合成设计提供了额外的机会。9 在一个例子中，环化的底物是通过邻位环己烯二醇的氧化裂解制备的
• Chemoselective synthesis of polyfunctional aminophenyl 2-oxobut-3-enyl - and quinolinylmethyl- C-glycopyranosides from nitrophenyl 2-oxobut-3-enyl C-glycopyranosides under ultrasonic vibration
  作者：K. Kumar G. Ramakrishna、Arya Ajay、Anindra Sharma、Rama P. Tripathi

  DOI：10.3998/ark.5550190.0014.213

  日期：——

  Chemoselective reduction of nitro group in polyfunc tional nitrophenyl 2-oxobut-3-enyl C- glycopyranosides to the respective aminophenyl 2-ox obut-3-enyl glycopyranosides with SnCl 2.2H 2O under ultrasonic vibration in good yields was ach ieved successfully. Other potentially reducible groups such as carbonyl, este r, azide, tosyl, alkenic substituents were unaffected during reaction. The 2 '-nitr

  在超声波振动下成功地实现了多功能硝基苯基 2-oxobut-3-enyl C-glycopyranosides 中硝基的化学选择性还原为相应的氨基苯基 2-ox obut-3-enyl glycopyranosides 和 SnCl 2.2H 2O。其他潜在的可还原基团，如羰基、酯、叠氮化物、甲苯磺酰基、烯基取代基在反应过程中不受影响。2'-硝基苯基-2-oxobut-3-enyl glycopyranosides 作为还原底物，通过还原和分子内环缩合反应得到 2-quinolinemethyl pyranosides。这些 β-C-吡喃糖苷在药物化学中具有广阔的前景。