3-O-allyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-O-(tert-butyldiphenylsilyl)-sn-glycerol | 1384160-42-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 3-O-allyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-O-(tert-butyldiphenylsilyl)-sn-glycerol
• CAS: 1384160-42-2
• 化学式: C₅₆H₆₄O₈Si
• 分子量: 893.205
• InChiKey: PZDYVMWLOYZLJV-WXZVUDQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.85
• 重原子数：
  65.0
• 可旋转键数：
  24.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  73.84
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-O-allyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-O-(tert-butyldiphenylsilyl)-sn-glycerol 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 为溶剂， 反应 6.0h， 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
• 作为产物：
  描述：

  3-O-allyl-2-O-[2,3,4-tri-O-benzyl-6-O-(9H-fluoren-9-ylmethyloxycarbohyl)-α-D-glucopyranosyl]-1-O-(tert-butyldiphenylsilyl)-sn-glycerol 在 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.25h， 生成 3-O-allyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-O-(tert-butyldiphenylsilyl)-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