Ethyl 2-O-benzoyl-3-O-benzyl-1-thio-α-D-arabinofuranoside | 282107-51-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 2-O-benzoyl-3-O-benzyl-1-thio-α-D-arabinofuranoside
• 英文别名: [(2R,3S,4R,5R)-2-ethylsulfanyl-5-(hydroxymethyl)-4-phenylmethoxyoxolan-3-yl] benzoate
• CAS: 282107-51-1
• 化学式: C₂₁H₂₄O₅S
• 分子量: 388.485
• InChiKey: HYUZQVQBNYWRLF-WERVVEIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  90.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 2-O-benzoyl-3-O-benzyl-1-thio-α-D-arabinofuranoside 在 咪唑 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-1-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  1,2,5-ortho esters of d-arabinose as versatile arabinofuranosidic building blocks. Concise synthesis of the tetrasaccharidic cap of the lipoarabinomannan of Mycobacterium tuberculosis

  摘要：

  研究发现，D-阿拉伯糖的1,2,5-邻醚酯在氧和硫亲核试剂的作用下开环后，是形成α和β阿拉伯呋喃糖苷键的理想手性砌块；随后，以高度汇聚的方式合成了结核分枝杆菌脂阿拉伯甘露聚糖的四糖帽。

  DOI：

  10.1039/b000873g
• 作为产物：
  描述：

  methyl tri-O-benzoyl-α-D-arabinofuranoside 在 1,1-二氯甲醚 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 sodium methylate 、 四氯化锡 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.5h， 生成 Ethyl 2-O-benzoyl-3-O-benzyl-1-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  Elaboration of Monoarabinofuranosidic Building Blocks

  摘要：

  DOI：

  10.1002/1099-0690(200211)2002:22<3864::aid-ejoc3864>3.0.co;2-8

文献信息

• Ring opening of acylated β-d-arabinofuranose 1,2,5-orthobenzoates with nucleophiles allows access to novel selectively-protected arabinofuranose building blocks
  作者：Nikita M. Podvalnyy、Sergey L. Sedinkin、Polina I. Abronina、Alexander I. Zinin、Ksenia G. Fedina、Vladimir I. Torgov、Leonid O. Kononov

  DOI：10.1016/j.carres.2010.11.002

  日期：2011.1

  beta-D-Arabinofuranose 1,2,5-orthobenzoates with 3-O-acetyl, 3-O-benzoyl, and 3-O-chloroacetyl groups were prepared in an efficient manner starting from readily available crystalline methyl 2,3,5-tri-O-benzoyl-alpha-D-arabinofuranoside, and ring-opening reactions of these compounds with O- and S-nucleophiles were studied. Optimized conditions leading to the formation of the respective monosaccharide adducts (up to 96% isolated yields) and to alpha-(1 -> 5)-linked disaccharide thioglycosides with 5'-OH unprotected (up to 30% isolated yields) were found. Basing on these results, a novel approach for effective differentiation of 3,5-diol system and 2-hydroxy group in arabinofuranose thioglycosides was proposed. The selectively protected derivatives prepared are valuable building blocks for the assembly of linear and branched oligoarabinofuranosides. (C) 2010 Elsevier Ltd. All rights reserved.
• A comprehensive glycosylation system for the elaboration of oligoarabinofuranosides
  作者：Sylvie Sanchez、Toufiq Bamhaoud、Jacques Prandi

  DOI：10.1016/s0040-4039(00)01273-9

  日期：2000.9

  1,2,5-Orthoesters of D-arabinose are key compounds for the construction of a glycosylation system that allows the stereoselective synthesis of any interglycosidic linkage between arabinofuranosidic units. Application to the synthesis of a pentaarabinofuranoside of the mycobacterial cell wall is also described. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis and TNF-α inducing activities of mycoloyl-arabinan motif of mycobacterial cell wall components
  作者：Akihiro Ishiwata、Hiroko Akao、Yukishige Ito、Makoto Sunagawa、Naoto Kusunose、Yasuo Kashiwazaki

  DOI：10.1016/j.bmc.2005.12.037

  日期：2006.5

  The extract of the cell wall skeleton of Bacillus Calmette-Guerin (BCG-CWS) from Mycobacterium bovis is known to be an activator of innate immunity. Synthesis of pentaarabinofuranoside as part of the arabinan moiety of BCG-CWS was achieved by double alpha-arabinofuranosylation followed by double beta-arabinofuranosylation with orthogonally protected donors. Mycolic esters of the arabinan in the terminal lipo-arabinan motif or BCG-CWS were synthesized through alkylation of unprotected mycolic acid with bis- and tetra-tosylates of pentaarabinofuranoside. A series Of compounds Were Subjected to a tumor necrosis factor alpha (TNF-alpha) secretion-inducing assay, disclosing aspects of the structure-activity relationship which Should be useful in finding the site of the activity. (c) 2005 Elsevier Ltd. All rights reserved.
• 1,2,5-ortho esters of d-arabinose as versatile arabinofuranosidic building blocks. Concise synthesis of the tetrasaccharidic cap of the lipoarabinomannan of Mycobacterium tuberculosis
  作者：Toufiq Bamhaoud、Sylvie Sanchez、Jacques Prandi

  DOI：10.1039/b000873g

  日期：——

  1,2,5-ortho esters of D-arabinose were found to be ideally suited building blocks for the stereoselective formation of α and β arabinofuranosidic linkages after nucleophilic opening of the orthoester with oxygen and sulfur nucleophiles; the tetrasaccharidic cap of the lipoarabinomannan of Mycobacterium tuberculosis was then synthesized in a highly convergent manner.

  研究发现，D-阿拉伯糖的1,2,5-邻醚酯在氧和硫亲核试剂的作用下开环后，是形成α和β阿拉伯呋喃糖苷键的理想手性砌块；随后，以高度汇聚的方式合成了结核分枝杆菌脂阿拉伯甘露聚糖的四糖帽。
• Elaboration of Monoarabinofuranosidic Building Blocks
  作者：Sylvie Sanchez、Toufiq Bamhaoud、Jacques Prandi

  DOI：10.1002/1099-0690(200211)2002:22<3864::aid-ejoc3864>3.0.co;2-8

  日期：2002.11