phenyl 3,5-di-O-(di-tert-butylsilylene)-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside | 1392213-73-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: phenyl 3,5-di-O-(di-tert-butylsilylene)-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside
• CAS: 1392213-73-8
• 化学式: C₂₈H₅₀O₄SSi₂
• 分子量: 538.94
• InChiKey: PTVYVJFIDWRPDZ-FXSWLTOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.52
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  phenyl 3,5-di-O-(di-tert-butylsilylene)-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside 、 2-chloroethyl 2-O-benzoyl-3,5-di-O-(3,5-di-O-benzoyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 17.67h， 以77%的产率得到2-chloroethyl 2-O-benzoyl-3,5-di-O-{3,5-di-O-benzoyl-2-O-[3,5-di-(tert-butylsilylene)-2-O-triisopropylsilyl-D-arabinofuranosyl]-α-D-arabinofuranosyl}-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of branched arabinofuranose pentasaccharide fragment of mycobacterial arabinans as 2-azidoethyl glycoside

  摘要：

  Branched arabinofuranose pentasaccharide with 2-azidoethyl aglycon was prepared for the first time by [3+1+1] bis-(1,2-cis)-glycosylation of trisaccharide diol with silyl-protected thioglycoside glycosyl donor. The presence of 2-azidoethyl aglycon would enable the preparation of neoglycoconjugates using the click chemistry approaches. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.05.021
• 作为产物：
  描述：

  phenyl 3,5-O-(di-tert-butylsilanediyl)-1-thio-α-D-arabinofuranoside 、 三异丙基硅基三氟甲磺酸酯 在 2,4,6-三甲基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以94%的产率得到phenyl 3,5-di-O-(di-tert-butylsilylene)-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of branched arabinofuranose pentasaccharide fragment of mycobacterial arabinans as 2-azidoethyl glycoside

  摘要：

  Branched arabinofuranose pentasaccharide with 2-azidoethyl aglycon was prepared for the first time by [3+1+1] bis-(1,2-cis)-glycosylation of trisaccharide diol with silyl-protected thioglycoside glycosyl donor. The presence of 2-azidoethyl aglycon would enable the preparation of neoglycoconjugates using the click chemistry approaches. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.05.021

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。
• Synthesis of a tetrasaccharide containing Janus aglycone related to the terminal fragment of polysaccharides of mycobacteria
  作者：P. I. Abronina、N. N. Malysheva、A. I. Zinin、L. O. Kononov

  DOI：10.1007/s11172-023-3870-7

  日期：2023.4

  A convergent synthesis of arabinofuranose-based, α-(1→5), β-(1→2)-linked tetrasaccharide related to the terminal fragment of lipoarabinomannan and arabinogalactan of mycobacteria was carried out. The tetrasaccharide was synthesized as a glycoside with 4-(2-azidoethoxy)phenyl aglycone belonging to the class of Janus aglycones, which can serve as both a temporary protective group of the anomeric position

  进行了与分枝杆菌的脂阿拉伯甘露聚糖和阿拉伯半乳聚糖末端片段相关的基于阿拉伯呋喃糖的 α-(1→5)、β-(1→2)-连接四糖的聚合合成。该四糖以糖苷的形式与属于 Janus 糖苷配基类的 4-(2-叠氮基乙氧基) 苯基糖苷配基合成，它既可以作为碳水化合物残基异头位置的临时保护基，也可以作为碳水化合物残基异头位置的（预）间隔基。新糖缀合物 (NGC) 的合成可用于开发新的结核病诊断剂。关键步骤是形成 1,2-顺式糖苷键。
• Synthesis of 4-(3-azidopropoxy)phenyl glycoside of tetraarabinofuranoside related to the terminal fragment of arabinogalactan and lipoarabinomannan of mycobacteria
  作者：P. I. Abronina、M. Yu. Karpenko、N. N. Malysheva、A. I. Zinin、I. V. Myachin、L. O. Kononov

  DOI：10.1007/s11172-024-4131-z

  日期：2024.1

  Abstract A convergent synthesis of tetraarabinofuranoside β-d-Araf-(1→2)-α-d-Araf-(1→3)-α-d-Araf-(1→5)-α-d-Araf-1↑OR (R is 4-(3-azidopropoxy)phenyl) related to the terminal fragment of lipoarabinomannan (LAM) and arabinogalactan of mycobacteria was developed. The synthesized tetraarabinofuranoside represents a linear motif of a branched hexaarabinofuranoside, which is the main LAM epitope. 4-(3-Azidopropoxy)phenyl

  摘要 四阿拉伯呋喃糖苷 β- d -Ara f -(1→2)-α- d -Ara f -(1→3)-α- d -Ara f -(1→5)-α- d -Ara f的收敛合成开发了与分枝杆菌的脂阿拉伯甘露聚糖（LAM）和阿拉伯半乳聚糖末端片段相关的-1↑OR（R为4-（3-叠氮基丙氧基）苯基）。合成的四阿拉伯呋喃糖苷代表支链六阿拉伯呋喃糖苷的线性基序，它是主要的 LAM 表位。4-(3-叠氮丙氧基)苯基苷元属于Janus苷元类，它既可以作为碳水化合物异头位置的临时保护基团，也可以作为合成新糖缀合物的（前）间隔基，可用于开发新的结核病诊断分析。合成的关键步骤是1,2-顺式糖苷键的形成。
• 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.