ethyl 2,3-di-O-benzyl-5-O-p-methoxybenzyl-1-thio-α-D-arabinofuranoside | 886852-29-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3-di-O-benzyl-5-O-p-methoxybenzyl-1-thio-α-D-arabinofuranoside
• CAS: 886852-29-5
• 化学式: C₂₉H₃₄O₅S
• 分子量: 494.652
• InChiKey: IPMIHAQOOAUSDV-OVHUPFAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  35.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 2,3-di-O-benzyl-5-O-p-methoxybenzyl-1-thio-α-D-arabinofuranoside 、 methyl 3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranoside 在 2,6-二叔丁基-4-甲基吡啶 、 3 A molecular sieve 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以82%的产率得到(2S,3S,3aR,9aR)-3-[(3S,4R,5R)-3,4-Bis-benzyloxy-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yloxy]-5,5,7,7-tetraisopropyl-2-methoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacyclooctene
  参考文献：
  名称：

  Stereoselective Synthesis of a Fragment of Mycobacterial Arabinan

  摘要：

  Strategies for the stereoselective synthesis of mycobacterial arabinan were explored. Arabinofuranosyl donors with various protective groups were screened in terms of suitability for beta-( 1,2- cis)- selective glycosylation. The protective group was found to affect the stereoselectivity of arabinofuranosylation. beta-Selectivity was drastically enhanced by using donors protected with 3,5- TIDPS, possibly due to conformational constraints on the furanose ring. Synthesis of heptaarabinofuranoside was then performed to demonstrate the practicality of this methodology.

  DOI：

  10.1021/ol062198j
• 作为产物：
  描述：

  Ethyl 2-O-benzoyl-3-O-benzyl-1-thio-α-D-arabinofuranoside 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 ethyl 2,3-di-O-benzyl-5-O-p-methoxybenzyl-1-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis and TNF-α inducing activities of mycoloyl-arabinan motif of mycobacterial cell wall components

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2005.12.037