p-cresyl 2-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1-thio-α-D-arabinofuranoside | 204918-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-cresyl 2-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1-thio-α-D-arabinofuranoside
• 英文别名: [(6aR,8R,9S,9aR)-8-(4-methylphenyl)sulfanyl-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl] benzoate
• CAS: 204918-58-1
• 化学式: C₃₁H₄₆O₆SSi₂
• 分子量: 602.94
• InChiKey: KLOTVDCHDSGTKJ-XHMHJBHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.99
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-cresyl 2-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1-thio-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.42h， 生成 octyl 2,3-di-O-benzoyl-5-O-(2,5-di-O-benzoyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of octyl arabinofuranosides as substrates for mycobacterial arabinosyltransferases

  摘要：

  A panel of octyl oligosaccharides comprised of arabinofuranose rings have been synthesized via efficient and readily scaleable routes. The key glycosylation reactions involved the coupling of octyl glycoside acceptors with the appropriate thioglycosides using N-iodosuccinimide and silver triflate activation. These syntheses were undertaken to provide substrates suitable for use in assays of mycobacterial arabinosyltransferases. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00541-4
• 作为产物：
  描述：

  1-(p-thiocresyl)-2,3,5-tri-O-acetyl-α-D-arabinofuranoside 在 吡啶 、 甲醇 、 sodium methylate 作用下， 生成 p-cresyl 2-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1-thio-α-D-arabinofuranoside
  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

文献信息

• Synthesis of Docosasaccharide Arabinan Motif of Mycobacterial Cell Wall
  作者：Akihiro Ishiwata、Yukishige Ito

  DOI：10.1021/ja109932t

  日期：2011.2.23

  Mycobacterial arabinan is a common constituent of both arabinogalactan (AG) and lipoarabinomannan (LAM). In this study, synthesis of β-Araf containing common arabinan docosasaccharide motif (22 Araf monomer units) of mycobacterial cell wall was achieved. Our synthetic strategy toward arabinan involves (1) the stereoselective β-arabinofuranosylation using both 3,5-O-TIPDS-protected and NAP-protected

  分枝杆菌阿拉伯聚糖是阿拉伯半乳聚糖 (AG) 和脂阿拉伯甘露聚糖 (LAM) 的常见成分。在这项研究中，合成了含有常见阿拉伯二十二糖基序（22 个 Araf 单体单元）的分枝杆菌细胞壁的 β-Araf。我们对阿拉伯聚糖的合成策略包括 (1) 立体选择性 β-阿拉伯呋喃糖基化，分别使用 3,5-O-TIPDS 保护和 NAP 保护的阿拉伯呋喃糖基供体进行直接的分子间糖基化和分子内苷元递送 (IAD)，以及 (2)收敛片段与线性序列上的分支片段偶联，使用硫糖苷供体，通过三步程序从每个片段的还原末端相应的丙酮化物获得。
• The synthesis of mycobacterial dimycoloyl diarabinoglycerol based on defined synthetic mycolic acids
  作者：Omar T. Ali、Mohsin O. Mohammed、Paul J. Gates、Mark S. Baird、Juma’a R. Al Dulayymi

  DOI：10.1016/j.chemphyslip.2019.01.002

  日期：2019.7

  and potentially valuable antigens in the serodiagnosis of mycobacterial infections. We now report the highly stereocontrolled synthesis of diacyl l-glycerol-(1'→1)-β-d-arabinofuranosyl-α-d-arabinofuranosides based on simple fatty acids and single defined synthetic mycolic acids. NMR analysis confirmed that the synthetic core was identical to that in natural mixtures.

  从分枝杆菌中分离出来的天然二甲酰氯二氮杂甘油的复杂混合物在分枝杆菌感染的血清学诊断中既是有效的免疫信号传导剂，又是潜在有价值的抗原。现在，我们报告基于简单脂肪酸和单一定义的合成霉菌酸，对二酰基L-甘油-（1'→1）-β-d-阿拉伯呋喃糖基-α-d-阿拉伯呋喃糖苷进行高度立体控制的合成。NMR分析证实合成核与天然混合物中的核相同。
• Silver-assisted gold-catalyzed solid phase synthesis of linear and branched oligosaccharides
  作者：Yogesh Sutar、Madhuri Vangala、Srinivas Hotha

  DOI：10.1039/d1cc06270k

  日期：——

  Unlike solid phase synthesis of peptides, synthesis of oligosaccharides by solid phase methods is lagging behind owing to inherent challenges faced while executing glycosidations. In this communication, silver-assisted gold-catalyzed glycosidations are found to be excellent for solid phase oligosaccharide synthesis. Glycosidations under catalytic conditions, one time coupling with four equivalents

  与肽的固相合成不同，由于在进行糖苷化时面临固有的挑战，通过固相方法合成寡糖处于滞后状态。在这篇通讯中，发现银辅助金催化的糖苷化对于固相寡糖合成非常有效。催化条件下的糖苷化、与四当量供体的一次偶联、25°C 下不到 30 分钟的反应以及甲硅烷基和苯甲酸酯保护基团的树脂脱保护是其显着特征。光裂解聚糖具有受保护的氨基官能团，可用于生物共轭。该方法的多功能性是通过合成线性和支化呋喃五阿拉伯糖苷而建立的。
• 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.
• Concise synthesis of an arabinofuranose hexasaccharide present in the cell wall of Mycobacterium tuberculosis
  作者：Karnakar C. Reddy、Narra Padmaja、Vibha Pathak、Ashish K. Pathak

  DOI：10.1016/j.tetlet.2012.03.016

  日期：2012.5

  Mycobacterium cell wall consists of three major polysaccharide portions and arabinofuranose (Araf) is present in two of the major portions, arabinogalactan (AG) and lipoarabinomannan (LAM). A peculiar Araf hexasaccharide possessing two beta-linked Araf units are present in both AG and LAM polysaccharides. Herein, we report an efficient and concise synthesis of this Araf hexasaccharide using single starting 3,5-TIPDS protected Araf thioglycoside precursor. Double beta-glycosylation was achieved using strained cyclic 2-p-methoxybenzyl-3,5-TIPDS Araf thioglycoside donor. (C) 2012 Elsevier Ltd. All rights reserved.