phenyl 2-O-benzyl-3,5-(ditert-butylsilanediyl)-1-thio-α-D-arabinofuranoside | 1096610-44-4

• 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: phenyl 2-O-benzyl-3,5-(ditert-butylsilanediyl)-1-thio-α-D-arabinofuranoside
• 英文别名: (4aR,6R,7S,7aR)-2,2-ditert-butyl-7-phenylmethoxy-6-phenylsulfanyl-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxasiline
• CAS: 1096610-44-4
• 化学式: C₂₆H₃₆O₄SSi
• 分子量: 472.721
• InChiKey: XINYRWUQWGOTBC-JLLPCOHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.55
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-benzyl-3,5-(ditert-butylsilanediyl)-1-thio-α-D-arabinofuranoside 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以60%的产率得到
  参考文献：
  名称：

  Synthesis of β-d-arabinofuranosides: stereochemical differentiation between d- and l-enantiomers

  摘要：

  The glycosylation of 3,5-O-di-tert-butylsilyene-protected D-thioarabinofuranosides with a range of glycosyl acceptors using NIS/AgOTf as promoters proceeded in a stereoselective manner to give the corresponding beta-D-arabinofuranosides in high yields. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.09.006
• 作为产物：
  描述：

  phenyl 3,5-O-(di-tert-butylsilanediyl)-1-thio-α-D-arabinofuranoside 、 溴甲苯 在 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以75%的产率得到phenyl 2-O-benzyl-3,5-(ditert-butylsilanediyl)-1-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of β-d-arabinofuranosides: stereochemical differentiation between d- and l-enantiomers

  摘要：

  The glycosylation of 3,5-O-di-tert-butylsilyene-protected D-thioarabinofuranosides with a range of glycosyl acceptors using NIS/AgOTf as promoters proceeded in a stereoselective manner to give the corresponding beta-D-arabinofuranosides in high yields. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.09.006

文献信息

• Synthesis of hexasaccharide fragment of lipoarabonomannan from Mycobacteria: advantages of the benzyl-free approach
  作者：N. M. Podvalnyy、P. I. Abronina、K. G. Fedina、N. N. Kondakov、A. I. Zinin、A. O. Chizhov、V. I. Torgov、V. V. Kachala、L. O. Kononov

  DOI：10.1007/s11172-015-0992-5

  日期：2015.5

  Spacered branched hexaarabinofuranoside, which corresponds to the terminal fragment of mycobacterial lipoarabinomannan and arabinogalactan, was synthesized via three different routes. Synthetic scheme which involved only acyl and silyl protective groups (benzyl-free approach) allows one to reduce the number of deprotection steps, enhance the overall yield, and keep the azido group until the end of the synthesis.

  通过三种不同的途径合成了空间支链六阿拉伯呋喃糖苷，该物质与分枝杆菌脂阿拉伯甘露聚糖和阿拉伯半乳聚糖的末端片段相对应。仅涉及酰基和硅基保护基团（不含苄基的方法）的合成方案可以减少脱保护步骤，提高总产量，并在合成结束时保留叠氮基。
• The use of O-trifluoroacetyl protection and profound influence of the nature of glycosyl acceptor in benzyl-free arabinofuranosylation
  作者：Polina I. Abronina、Ksenia G. Fedina、Nikita M. Podvalnyy、Alexander I. Zinin、Alexander O. Chizhov、Nikolay N. Kondakov、Vladimir I. Torgov、Leonid O. Kononov

  DOI：10.1016/j.carres.2014.05.017

  日期：2014.9

  The influence of O-trifluoroacetyl (TFA) groups at different positions of thioglycoside glycosyl donors on stereoselectivity of α-arabinofuranosylation leading to corresponding disaccharides was studied. It was shown that TFA group in thioglycoside glycosyl donors, when combined with 2-O-(triisopropylsilyl) (TIPS) non-participating group, may be regarded as an electron-withdrawing protecting group that may enhance 1,2-cis-selectivity in arabinofuranosylation, the results strongly depending on the nature of glycosyl acceptor. The reactivities of the glycosyl donors were compared with those of a similar thioglycoside with O-pentafluoropropionyl groups and the known phenyl 3,5-O-(di-tert-butylsilylene)-1-thio-α-d-arabinofuranosides with 2-O-TIPS and 2-O-benzyl groups. The 'matching' in the donor-acceptor combination was found to be critical for achieving both high reactivity of glycosyl donor and β-stereoselectivity of arabinofuranosylation. The use of glycosyl donors with TFA and silyl protection may be useful in the realization of the benzyl-free approach to oligoarabinofuranosides with azido group in aglycon-convenient building blocks for the preparation of neoglycoconjugates.
• Synthesis of covalent conjugates of hexaarabinofuranoside with proteins and their testing as antigens for serodiagnosis of tuberculosis
  作者：P. I. Abronina、N. M. Podvalnyy、T. M. Mel’nikova、A. I. Zinin、K. G. Fedina、V. V. Kachala、V. I. Torgov、L. O. Kononov、E. A. Panfertsev、E. V. Baranova、V. V. Mochalov、V. I. Dyatlova、S. F. Biketov

  DOI：10.1007/s11172-010-0397-4

  日期：2010.12
• Synthesis of β-d-arabinofuranosides: stereochemical differentiation between d- and l-enantiomers
  作者：Yingxi Wang、Samuel Maguire-Boyle、Ravindra T. Dere、Xiangming Zhu

  DOI：10.1016/j.carres.2008.09.006

  日期：2008.12

  The glycosylation of 3,5-O-di-tert-butylsilyene-protected D-thioarabinofuranosides with a range of glycosyl acceptors using NIS/AgOTf as promoters proceeded in a stereoselective manner to give the corresponding beta-D-arabinofuranosides in high yields. (C) 2008 Elsevier Ltd. All rights reserved.