5,6,7,9-tetra-O-acetyl-4,8-anhydro-1,3-dideoxy-D-glycero-D-galacto-non-2-ulose | 1004322-62-6

• 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: 5,6,7,9-tetra-O-acetyl-4,8-anhydro-1,3-dideoxy-D-glycero-D-galacto-non-2-ulose
• 英文别名: 1-(2',3',4',6'-tetra-O-acetyl-β-D-mannopyranosyl)-propan-2-one；1-(2,3,4,6-tetra-O-acetyl-β-D-mannosyl)propan-2-one；[(2R,3R,4R,5R,6S)-3,4,5-triacetyloxy-6-(2-oxopropyl)oxan-2-yl]methyl acetate
• CAS: 1004322-62-6
• 化学式: C₁₇H₂₄O₁₀
• 分子量: 388.372
• InChiKey: DWRNVUXNLZJUGM-MZBWOGCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5,6,7,9-tetra-O-acetyl-4,8-anhydro-1,3-dideoxy-D-glycero-D-galacto-non-2-ulose 在 四氢吡咯 、 tin(II) chloride dihdyrate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (E)-1-[3-(p-toluenesulfonamido)phenyl]-4-[1′-deoxy-2′,3′,4′,6′-tetra-O-acetyl-β-D-manno-pyranos-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：

  乙酸酐 、 4,8-anhydro-1,3-dideoxy-D-glycero-D-galacto-nonulose 在 吡啶 作用下， 以100%的产率得到5,6,7,9-tetra-O-acetyl-4,8-anhydro-1,3-dideoxy-D-glycero-D-galacto-non-2-ulose
  参考文献：
  名称：

  Diastereoselective addition of sugar radicals to camphorsultam glyoxilic oxime ether: a route toward C-glycosylthreonine and allothreonine

  摘要：

  C-葡萄糖基、甘露糖基和半乳糖基2-碘丙烷很容易从相应的C-糖基酮获得，与(+)-或(-)-樟脑磺内酰胺乙醛酸肟醚偶联，非对映选择性范围为70:30至80:20。 C-葡萄糖基别苏氨酸通过樟脑磺内酰胺部分的裂解获得。

  DOI：

  10.1039/b910050d

文献信息

• Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases
  作者：Leonardo E. Riafrecha、Oscar M. Rodríguez、Daniela Vullo、Claudiu T. Supuran、Pedro A. Colinas

  DOI：10.1016/j.bmc.2012.09.002

  日期：2013.3

  glycosides incorporating the phenol moiety has been prepared by reaction of glycosyl ketones with the appropriate benzaldehydes. Glycosides were tested for the inhibition of twelve mammalian isoforms of carbonic anhydrase. This is the first study in which α-CAs have been investigated for their interaction with C-glycosides, a novel carbohydrate scaffold in the design of carbonic anhydrase inhibitors. The

  通过使糖基酮与适当的苯甲醛反应，已经制备了少量的结合有酚部分的C-肉桂酰基糖苷。测试了糖苷对十二种碳酸酐酶哺乳动物同工型的抑制作用。这是首次研究α-CA与C-糖苷的相互作用的研究，C-糖苷是碳酸酐酶抑制剂设计中的新型碳水化合物支架。该ç-肉桂酰基糖苷通常是有效的CA抑制剂，对CA I，II，IV，VA，VB，VI，VII，IX，XII，XIII，XIV和无效的CA III抑制剂的抑制常数在低微摩尔范围内。这些结果证实，将碳水化合物部分连接至CA酚药效团改善了其抑制活性。
• New and general synthesis of β-C-glycosylformaldehydes from easily available β-C-glycosylpropanones
  作者：Stéphanie Norsikian、Jennifer Zeitouni、Stéphanie Rat、Sylvie Gérard、André Lubineau

  DOI：10.1016/j.carres.2007.09.002

  日期：2007.12

  A highly effective method for the introduction of a formyl group at the anomeric position of pyranosides was developed via enolisation Of beta-C-D-glycopyranosylpropan-2-one using thermodynamic conditions then oxidative cleavage of the more substituted double bond. This sequence affords the desired aldehydes that are conveniently protected as aminals for purification and storage and easily regenerated using Dowex resin H+. In this paper, the syntheses of nine differently protected aldehydes derived from D-glucose, D-galactose. lactose and N-acetyl-D-glucosamine are presented. Our strategy proved to be very efficient in most cases excepted in the D-mannose series. (C) 2007 Elsevier Ltd. All rights reserved.
• Aldol reaction of β-C-glycosylic ketones: synthesis of C-(E)-cinnamoyl glycosylic compounds as precursors for new biologically active C-glycosides
  作者：Surendra Singh Bisht、Jyoti Pandey、Anindra Sharma、Rama Pati Tripathi

  DOI：10.1016/j.carres.2008.04.021

  日期：2008.7

  A series of beta-C-glycosylic ketones were prepared starting from D-glucose, D-xylose, D-mannose, and cellobiose. The beta-C-glycosylic ketones on aldol condensation with different aromatic aldehydes in the presence of a suitable organocatalyst led to the formation of respective C-(E)-cinnamoyl glycosides stereoselectively in good yields as precursors for the synthesis of biologically active compounds. (C) 2008 Elsevier Ltd. All rights reserved.