methyl 2-O-benzoyl-α-D-arabinofuranoside | 204918-53-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-benzoyl-α-D-arabinofuranoside
• 英文别名: methyl-2-O-benzoyl-α-D-Araf；[(2S,3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-methoxyoxolan-3-yl] benzoate
• CAS: 204918-53-6
• 化学式: C₁₃H₁₆O₆
• 分子量: 268.266
• InChiKey: XMMMJMUCTUYMGE-DCQANWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-O-benzoyl-α-D-arabinofuranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 Benzoic acid (2S,3S,4R,5R)-4-((2R,3S,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-5-hydroxymethyl-2-methoxy-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthetic arabinofuranosyl oligosaccharides as Mycobacterial arabinosyltransferase substrates

  摘要：

  A series of arabinofuranosyl oligosaccharides found as constituent parts of the polysaccharide portion of the cell wall of Mycobacterium tuberculosis have been chemically synthesized. Screening of these oligosaccharides as substrates for arabinosyltransferases present in mycobacterial membrane preparations suggests that modified oligosaccharide analogs as small as disaccharides may be inhibitors of glycan biosynthesis. Such inhibitors would be of potential utility as lead compounds in the identification of new drugs for the treatment of mycobacterial infections. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00049-3
• 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 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 24.5h， 生成 methyl 2-O-benzoyl-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

• Preparation of the tri-arabino di-mycolate fragment of mycobacterial arabinogalactan from defined synthetic mycolic acids
  作者：Mohsin O. Mohammed、Juma'a R. Al Dulayymi、Mark S. Baird

  DOI：10.1016/j.carres.2016.11.006

  日期：2017.1

  An efficient synthetic approach to tri-arabino di-mycolates, using structurally defined synthetic alpha-, keto and methoxy mycolic acids is described.

  描述了一种有效的合成方法，使用结构上定义的合成α-，酮和甲氧基霉菌酸合成三阿拉伯糖基二霉菌酸酯。
• Arabinofuranosyl Oligosaccharides from Mycobacteria:  Synthesis and Effect of Glycosylation on Ring Conformation and Hydroxymethyl Group Rotamer Populations
  作者：Francis W. D'Souza、Joseph D. Ayers、Patrick R. McCarren、Todd L. Lowary

  DOI：10.1021/ja993543l

  日期：2000.2.1

  A series of alpha-D-arabinofurnnosyl oligosaccharides (2-8) that an fragments of the arabinan portions of two polysaccharides present in the cell wall of Mycobacterium tuberculosis have been synthesized. Preparation of the oligosaccharides involved the sequential addition of arabinofuranosyl residues from thioglycoside donors to methyl glycoside accepters. High-resolution NMR studies on the final products provided all (3)J(H,H) values, which were in turn used in PSEUROT 6.2 calculations to determine both the identity and equilibrium populations of preferred conformers for each furanose ring in these glycans. Comparison of the ring conformers present in 2-8 with these available in the parent monosaccharide, methyl alpha-D-arabinofuranose (16), allowed the determination of the effect of glycosylation upon ring conformation. At equilibrium, 16 exists as an approximately equimolar mixture of T-0(4) (North, N) and T-2(3) (South, S) conformers. These studies showed that glycosylation of 16 at OH5 resulted in no significant change in conformer identity or population relative to 16. However, glycosylation of OH3 resulted in a change in the identity of the N species (to E-O) and a significant favoring of this conformer at equilibrium. These trends were seen in all of the oligosaccharides. The populations of the three possible staggered rotamers (gg, gt, tg) about the C4-C5 bond were essentially the same for all residues in 2-8, and thus this equilibrium does not appear to be sensitive to glycosylation.