2,3-di-O-benzyl-1-(p-tolylthio)-1-deoxy-α-D-arabinofuranoside | 920281-46-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-di-O-benzyl-1-(p-tolylthio)-1-deoxy-α-D-arabinofuranoside
• 英文别名: p-tolyl 2,3-O-dibenzyl-1-thio-α-D-arabinofuranoside
• CAS: 920281-46-5
• 化学式: C₂₆H₂₈O₄S
• 分子量: 436.572
• InChiKey: QZKNHBGJBBSFIK-FXSWLTOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzyl-1-(p-tolylthio)-1-deoxy-α-D-arabinofuranoside 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 2,4,6-三叔丁基嘧啶 、 3,5-di(trifluoromethyl)phenyl(cyano)iodonium triflate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 p-methoxyphenyl (2,3-di-O-benzyl-5-O-picolinoyl-α-D-arabinofuranosyl)-(1→4)-2-azido-3-O-benzoyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  3,5-二（三氟甲基）苯基（氰基）碘鎓三氟甲磺酸盐作为对甲苯基硫糖苷供体的新型潜在活化剂

  摘要：

  3,5-二（三氟甲基）苯基（氰基）碘鎓三氟甲磺酸盐被描述为一种易于获取、稳定且功能强大的亲硫试剂，可以在室温下激活一批对甲苯基硫苷供体。各种醇受体被有效地糖基化，提供所需的糖苷。新的激活协议具有温和的条件以及与一些经典策略的高度兼容性，用于一些生物学相关糖苷键的立体选择性构建，例如 α-idosides、α-galactoamines、β-mannosides 和 β-rhamnosides。

  DOI：

  10.1039/d2ob01940j
• 作为产物：
  描述：

  p-tolyl 5-O-t-butyldiphenylsilyl-1-thio-α-D-arabinofuranoside 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2,3-di-O-benzyl-1-(p-tolylthio)-1-deoxy-α-D-arabinofuranoside
  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

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。
• General Homologation Strategy for Synthesis of <scp>l</scp>-<i>glycero</i>- and <scp>d</scp>-<i>glycero</i>-Heptopyranoses
  作者：Shaheen K. Mulani、Kuang-Chun Cheng、Kwok-Kong T. Mong

  DOI：10.1021/acs.orglett.5b02620

  日期：2015.11.20

  A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed a-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.
• Probing the Effect of Acylation on Arabinofuranose Ring Conformation in Di- and Trisaccharide Fragments of Mycobacterial Arabinogalactan
  作者：Chunjuan Liu、Michele R. Richards、Todd L. Lowary

  DOI：10.1021/jo100575a

  日期：2010.8.6

  A major component of the cell wall of mycobacteria is the mycolyl-arabinogalactan (mAG) complex. The arabinose and galactose residues in mAG are found solely in the furanose form, and it has been suggested that the flexibility of these five-membered rings allows for the tight packing of mycolic acids. In order to probe the "flexible scaffold hypothesis", we designed and synthesized glycolipids 3-6 and 8-11 as simple models of the terminal portion of mAG. A set of donors and acceptors were explored for preparing the key beta-(1 -> 2) linkage in 2-6, and the best selectivity and yield can be obtained by using the electron-rich thioglycoside donor 14 and the O-5 p-methoxybenzyl-protected acceptor 17. Both alpha-linkages in the trisaccharides 7-11 were formed in a one-pot reaction. The conformations of compounds 2-11 were studied using solution-state NMR spectroscopy, but little change was observed in the coupling constants for the ring protons between 2 and 3-6 or between 7 and 8-11. However, the rotamer populations about the C-4-C-5 bond for the beta-linked ring in disaccharide 2 did change upon acylation at O-5.
• Synthesis of arabinofuranosides via low-temperature activation of thioglycosides
  作者：Haifeng Yin、Todd L Lowary

  DOI：10.1016/s0040-4039(01)01133-9

  日期：2001.8

  The synthesis of oligosaccharides containing arabinofuranose residues is reported. Coupling of thioglycoside donors 4, 6, or 7 and with acceptors 8-17 using N-iodosuccinimide and silver triflate activation provided glycosides with varying degrees of stereocontrol. (C) 2001 Elsevier Science Ltd. All rights reserved.