4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[β-D-arabinofuranosyl]-α-D-arabinofuranoside | 1621691-95-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[β-D-arabinofuranosyl]-α-D-arabinofuranoside
• CAS: 1621691-95-9
• 化学式: C₃₂H₃₃ClO₁₂
• 分子量: 645.06
• InChiKey: HACVCHWXZBIIRB-ONHIGNMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  45.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  159.44
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[β-D-arabinofuranosyl]-α-D-arabinofuranoside 在 sodium azide 、 18-冠醚-6 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.17h， 生成 4-(2-azidoethoxy)phenyl 2-O-(β-D-arabinofuranosyl)-α-D-arabinofuranoside
  参考文献：
  名称：

  The use of O-trifluoroacetyl protection and profound influence of the nature of glycosyl acceptor in benzyl-free arabinofuranosylation

  摘要：

  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.

  DOI：

  10.1016/j.carres.2014.05.017
• 作为产物：
  描述：

  4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[D-arabinofuranosyl]-α-D-arabinofuranoside 在 Sialsorb 600 (7.5 μm) column 作用下， 以 氯仿 、 异丙醇 、 Petroleum ether 为溶剂， 以53 mg的产率得到4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[β-D-arabinofuranosyl]-α-D-arabinofuranoside
  参考文献：
  名称：

  The use of O-trifluoroacetyl protection and profound influence of the nature of glycosyl acceptor in benzyl-free arabinofuranosylation

  摘要：

  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.

  DOI：

  10.1016/j.carres.2014.05.017

文献信息

• Five Triisopropylsilyl Substituents in Ara‐β‐(1→2)‐Ara Disaccharide Glycosyl Donor Make Unselective Glycosylation Reaction Stereoselective
  作者：Polina I. Abronina、Nelly N. Malysheva、Elena V. Stepanova、Julia S. Shvyrkina、Alexander I. Zinin、Leonid O. Kononov

  DOI：10.1002/ejoc.202201110

  日期：2022.12.12

  in arabinans from Mycobacterium tuberculosis using differently protected Ara-β-(1→2)-Ara disaccharide glycosyl donors in the absence of a participating group at O-2 was studied. The influence of the nature of the protective and leaving groups in glycosyl donors on the efficiency and stereoselectivity of the 1,2-trans-arabinofuranosylation was investigated. The efficiency of Ara-β-(1→2)-Ara p-tolyl thioglycoside

  研究了在 O-2 不存在参与组的情况下，使用不同保护的 Ara-β-(1→2)-Ara 二糖糖基供体在来自结核分枝杆菌的阿拉伯聚糖中形成 1,2-反式-阿拉伯呋喃糖苷键。研究了糖基供体中保护基团和离去基团的性质对 1,2-反式-阿拉伯呋喃糖基化的效率和立体选择性的影响。首次展示了含有五个三异丙基甲硅烷基的 Ara-β-(1→2)-Ara 对甲苯基硫糖苷在 1,2-反式立体选择性合成对应于 M. tuberculosis arabinan 片段的受保护四糖中的效率时间。相反，使用仅含有苯甲酰基或甲硅烷基和苯甲酰基的基于 Ara-β-(1→2)-Ara 的糖基供体导致立体控制的丧失。