phenyl 3,5-O-(di-tert-butylsilanediyl)-1-thio-α-D-arabinofuranoside | 1096610-41-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl 3,5-O-(di-tert-butylsilanediyl)-1-thio-α-D-arabinofuranoside
• 英文别名: phenyl 3,5-di-O-(di-tertbutylsilylene)-1-thio-α-D-arabinofuranoside；phenyl 3,5-O-(di-tert-butylsilylene)-1-thio-α-D-arabinofuranoside；(4aR,6R,7S,7aS)-2,2-ditert-butyl-6-phenylsulfanyl-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-7-ol
• CAS: 1096610-41-1
• 化学式: C₁₉H₃₀O₄SSi
• 分子量: 382.596
• InChiKey: AJVXLPRUCGFYFL-YYIAUSFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  二叔丁基硅基双(三氟甲烷磺酸) 、 phenyl 1-thio-α-D-arabinofuranoside 在 2,6-二甲基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以86%的产率得到phenyl 3,5-O-(di-tert-butylsilanediyl)-1-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  Efficient one-pot syntheses of α-d-arabinofuranosyl tri- and tetrasaccharides present in cell wall polysaccharide of Mycobacterium tuberculosis

  摘要：

  Two alpha-D-arabinofuramosyl oligosaccharides (2 and 3) found as constituent parts of the polysaccharide portion from the cell wall of Mycobacterium tuberculosis have been efficiently synthesized via a one-pot glycosylation procedure in which a key step is the chemoselective activation between D-arabinofuranosyl trichloroacetimidate donor 4 and partially protected aryl thioglycosides 5 or 7, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.038

文献信息

• 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 branched arabinofuranose pentasaccharide fragment of mycobacterial arabinans as 2-azidoethyl glycoside
  作者：Ksenia G. Fedina、Polina I. Abronina、Nikita M. Podvalnyy、Nikolay N. Kondakov、Alexander O. Chizhov、Vladimir I. Torgov、Leonid O. Kononov

  DOI：10.1016/j.carres.2012.05.021

  日期：2012.8

  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.