methyl 2,3-di-O-benzyl-5-dehydro-α-D-arabinofuranoside | 697298-48-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-5-dehydro-α-D-arabinofuranoside
• 英文别名: (2S,3S,4S,5S)-5-methoxy-3,4-bis(phenylmethoxy)oxolane-2-carbaldehyde
• CAS: 697298-48-9
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: JTXNKKPJPHUEOZ-ZRNYENFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-5-dehydro-α-D-arabinofuranoside 在 platinum(IV) oxide 氢气 、 sodium hydride 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 methyl 2,3-di-O-benzyl-5-deoxy-5-diethylphosphonomethyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Stereoselective synthesis of 5-methylphosphono-D-arabino hydroximolactone, inhibitor of glucosamine-6-phosphate synthase and phosphoglucose isomerase

  摘要：

  Compound 2, synthesized from D-arabinose in 12 steps with an overall 4% yield, is a competitive inhibitor vs fructose-6P for both phosphoglucose isomerase and glucosamine-6P synthase. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10514-7
• 作为产物：
  描述：

  阿拉伯糖 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 、 戴斯-马丁氧化剂 、 溶剂黄146 、 乙酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 methyl 2,3-di-O-benzyl-5-dehydro-α-D-arabinofuranoside
  参考文献：
  名称：

  对映体合成的磷脂酶A2抑制剂（-）-cinatrin B.

  摘要：

  描述了从D-阿拉伯糖衍生物9首次合成磷脂酶A2（PLA2）抑制剂（-）-cinatrin B（2）的对映体。螺内酯系统是由烯丙酯8的Ireland-Claisen重排，然后进行水解和立体选择性碘内酯化而形成的。通过烯丙基醇片段中的不对称性来控制重排的立体选择性。酯（S）-8分别以73∶27的比例高产率地得到所需的重排产物7和差向异构体13。通过螯合控制地将衍生自三甲基甲硅烷基乙炔的格利雅试剂加入到α-羟基酮6中，引入C2的最终立体中心。将末端炔烃转化为甲酯21，然后进行乙缩醛水解和选择性的乳糖醇氧化，得到肉桂酸B甲酯。 （22）。

  DOI：

  10.1021/jo016221k

文献信息

• Side Chain Conformation and Its Influence on Glycosylation Selectivity in Hexo- and Higher Carbon Furanosides
  作者：Sameera Siyabalapitiya Arachchige、David Crich

  DOI：10.1021/acs.joc.1c02374

  日期：2022.1.7

  arising from participation by the various benzyl ethers. The increased importance of ether participation in the furanoside series compared to the pyranosides is discussed in terms of the reduced stabilization afforded to furanosyl oxocarbenium ions by covalent triflate formation. The stereoselectivities of the four donors are discussed on the basis of the benzyl ether participation model.

  我们描述了一系列四种 6-deoxy-2,3,5-tri- O -benzyl hexofuranosyl供体的合成和侧链构象分析，其中d -gluco 、l -ido、d -altro 和l-半乳糖配置。这些化合物的环外键的构象取决于侧链与环的连接点和两个侧翼中心的相对构型，并且可以在此基础上类似于庚吡喃糖类似物进行预测。活化供体的变温核磁共振 (VT NMR) 光谱揭示了复杂的、依赖于构型的中间体混合物，我们将其解释为由各种苄醚参与产生的稠合和桥接的氧鎓离子。与吡喃糖苷相比，醚参与呋喃糖苷系列的重要性增加，讨论了通过共价三氟甲磺酸酯形成对呋喃糖基氧碳鎓离子提供的稳定性降低。
• Synthesis and kinetic evaluation of 4-deoxy-4-phosphonomethyl-d-erythronate, the first hydrolytically stable and potent competitive inhibitor of ribose-5-phosphate isomerase
  作者：Emmanuel Burgos、Laurent Salmon

  DOI：10.1016/j.tetlet.2004.03.004

  日期：2004.4

  4-deoxy-4-Phosphonomethyl-D-erythronate, an isosteric and hydrolytically stable analogue of the known ribose-5-phosphate isomerase inhibitor 4-deoxy-4-phospho-D-erythronate, was obtained by a 14-step synthesis from D-arabinose through a phosphate isomerase inhibitor 4-deoxy-4-D-erythronate, was obtained by a 14-step synthesis from D-arabinose through a highly improved Synthesis of the precursor 5-deoxy-5-phosphonomethyl-D-arabinose. The title compound appears as the first stable and potent competitive inhibitor of the enzyme catalyzed isomerization of ribose-5-phosphate to D-ribulose-5-phosphate (K-i = 74 muM. K-m/K-i = 100). exhibiting only a 3-fold weaker inhibitory activity than its phosphate analogue. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of C-disaccharide analogues of the α-d-arabinofuranosyl-(1→5)-α-d-arabinofuranosyl motif of mycobacterial cell walls via alkynyl intermediates
  作者：Tashfeen Aslam、Michael G.G. Fuchs、Adeline Le Formal、Richard H. Wightman

  DOI：10.1016/j.tetlet.2005.03.017

  日期：2005.5

  Two C-glycosides related to the recurrent alpha-D-arabinofuranosyl-(1 -> 5)-alpha-D-arabinofuranosyl structural motif of mycobacterial arabinan have been prepared by routes involving acetylenic intermediates. (c) 2005 Elsevier Ltd. All rights reserved.
• Enantiospecific Synthesis of the Phospholipase A₂ Inhibitor (−)-Cinatrin B
  作者：Anthony N. Cuzzupe、Romina Di Florio、Mark A. Rizzacasa

  DOI：10.1021/jo016221k

  日期：2002.6.1

  stereocenter at C2 was introduced via a chelation-controlled addition of the Grignard reagent derived from trimethylsilylacetylene to alpha-hydroxy ketone 6. Transformation of the terminal alkyne into the methyl ester 21 followed by acetal hydrolysis and selective lactol oxidation afforded cinatrin B methyl ester (22). Base hydrolysis and acid-induced relactonization then gave (-)-cinatrin B (2).

  描述了从D-阿拉伯糖衍生物9首次合成磷脂酶A2（PLA2）抑制剂（-）-cinatrin B（2）的对映体。螺内酯系统是由烯丙酯8的Ireland-Claisen重排，然后进行水解和立体选择性碘内酯化而形成的。通过烯丙基醇片段中的不对称性来控制重排的立体选择性。酯（S）-8分别以73∶27的比例高产率地得到所需的重排产物7和差向异构体13。通过螯合控制地将衍生自三甲基甲硅烷基乙炔的格利雅试剂加入到α-羟基酮6中，引入C2的最终立体中心。将末端炔烃转化为甲酯21，然后进行乙缩醛水解和选择性的乳糖醇氧化，得到肉桂酸B甲酯。 （22）。
• Stereoselective synthesis of 5-methylphosphono-D-arabino hydroximolactone, inhibitor of glucosamine-6-phosphate synthase and phosphoglucose isomerase
  作者：Corentin Le Camus、Alexia Chassagne、Marie-Ange Badet-Denisot、Bernard Badet

  DOI：10.1016/s0040-4039(97)10514-7

  日期：1998.1

  Compound 2, synthesized from D-arabinose in 12 steps with an overall 4% yield, is a competitive inhibitor vs fructose-6P for both phosphoglucose isomerase and glucosamine-6P synthase. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.