[2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-(2S)-1-glyceryl] 2-cyanoethyl N,N-diisopropylphosphoramidite | 1384160-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: [2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-(2S)-1-glyceryl] 2-cyanoethyl N,N-diisopropylphosphoramidite
• 英文别名: 3-[[(2S)-3-[bis(4-methoxyphenyl)-phenylmethoxy]-2-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropoxy]-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• CAS: 1384160-48-8
• 化学式: C₆₇H₇₇N₂O₁₁P
• 分子量: 1117.33
• InChiKey: FHTGNNAKLVRGGT-HDQDCJDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  81
• 可旋转键数：
  32
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-(2S)-1-glyceryl] 2-cyanoethyl N,N-diisopropylphosphoramidite 、 [(2R)-3-[2-cyanoethoxy-[(2S)-3-[2-cyanoethoxy-[(2S)-3-[2-cyanoethoxy-[(2S)-3-[2-cyanoethoxy-[(2S)-3-hydroxy-2-phenylmethoxypropoxy]-oxidophosphaniumyl]oxy-2-phenylmethoxypropoxy]-oxidophosphaniumyl]oxy-2-phenylmethoxypropoxy]-oxidophosphaniumyl]oxy-2-phenylmethoxypropoxy]-oxidophosphaniumyl]oxy-2-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropyl] 4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecylamino)-4-oxobutanoate 在 4,5-二氰基咪唑 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成
  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：

  2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 氢气 、 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 为溶剂， 反应 10.17h， 生成 [2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3-O-(4,4'-dimethoxytrityl)-(2S)-1-glyceryl] 2-cyanoethyl N,N-diisopropylphosphoramidite
  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

• Light fluorous synthesis of glucosylated glycerol teichoic acids
  作者：W.F.J. Hogendorf、A. Kropec、D.V. Filippov、H.S. Overkleeft、J. Huebner、G.A. van der Marel、J.D.C. Codée

  DOI：10.1016/j.carres.2012.02.023

  日期：2012.7

  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.