(3R,4S,5R,6R)-6-(((((9H-fluoren-9-yl)methoxy)carbonyl)oxy)methyl)-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-yl 2,2,2-trifluoro-N-phenylacetimidate | 1384160-41-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (3R,4S,5R,6R)-6-(((((9H-fluoren-9-yl)methoxy)carbonyl)oxy)methyl)-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-yl 2,2,2-trifluoro-N-phenylacetimidate
• CAS: 1384160-41-1
• 化学式: C₅₀H₄₄F₃NO₈
• 分子量: 843.896
• InChiKey: QGDZJXPIKMBKBY-VEWVWOIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.74
• 重原子数：
  62.0
• 可旋转键数：
  15.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  94.04
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R,6R)-6-(((((9H-fluoren-9-yl)methoxy)carbonyl)oxy)methyl)-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-yl 2,2,2-trifluoro-N-phenylacetimidate 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 三氟甲磺酸 、 氢气 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 6.67h， 生成 2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-O-(tert-butyldiphenylsilyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol
  参考文献：
  名称：

  Light fluorous synthesis of glucosylated glycerol teichoic acids

  摘要：

  We here describe the synthesis of glucosylated teichoic acid (TA) fragments using two complementary fluorous scaffolds. The use of a perfluorooctylpropylsulfonylethyl (F-Pse) linker in combination with (glucosyl) glycerol phosphoramidite building blocks allows for the assembly of TA fragments with a terminal phosphate mono-ester, whereas the use of a perfluorooctylsuccinyl spacer delivers TA oligomers featuring a terminal alcohol functionality. These complementary linker systems have been developed because the nature of the TA chain terminus can play a role in the biological activity of the synthetic TAs. A novel alpha-glucosylated glycerolphosphoramidite building block is introduced to allow for a robust light fluorous synthetic protocol. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.02.023

文献信息

• Stereoselective Synthesis of 2,3-Diamino-2,3-dideoxy-β-<scp>d</scp>-mannopyranosyl Uronates
  作者：Marthe T. C. Walvoort、Gert-Jan Moggré、Gerrit Lodder、Herman S. Overkleeft、Jeroen D. C. Codée、Gijsbert A. van der Marel

  DOI：10.1021/jo201179p

  日期：2011.9.16

  With the aim to find an efficient synthetic procedure for the construction of 2,3-diamino-2,3-dideoxy-beta-D-mannuronic acids, we evaluated three mannosyl donors: (S)-phenyl 4,6-di-O-acetyl-2,3-diazido mannopyranoside, (S)-phenyl 2,3-diazido-4,6-O-benzylidene mannopyranoside, and (S)-phenyl 2,3-diazido mannopyranosyl methyl uronate. The first two mannosylating agents are rather unselective or slightly a-selective in their condensation with three different acceptors. The mannuronic acid donor on the other hand reliably provides the desired beta-mannosidic linkage. A mechanistic rationale is put forward to account for the different behavior of the three donor types. Suitably protected 2,3-diazido mannuronic acids were employed to construct the all-cis-linked tetrasaccharide repeating unit of the capsular polysaccharide of Bacillus stearothermophilus, featuring two 2,3-diacetamido-2,3-dideoxy-beta-D-mannuronic acids.