p-tolyl 4-O-benzoyl-2-O-benzyl-1-thio-β-L-fucopyranoside | 1607433-71-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 4-O-benzoyl-2-O-benzyl-1-thio-β-L-fucopyranoside
• 英文别名: [(2S,3S,4R,5S,6R)-4-hydroxy-2-methyl-6-(4-methylphenyl)sulfanyl-5-phenylmethoxyoxan-3-yl] benzoate
• CAS: 1607433-71-5
• 化学式: C₂₇H₂₈O₅S
• 分子量: 464.582
• InChiKey: MCKHTFDJUDUJJT-YXEUDQQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  90.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-tolyl 4-O-benzoyl-2-O-benzyl-1-thio-β-L-fucopyranoside 在 吡啶 、 2,4,6-三甲基吡啶 、 N-碘代丁二酰亚胺 、 硫脲 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 25.33h， 生成 p-methoxyphenyl 4-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl-(1→3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Concise synthesis of the tetrasaccharide repeating unit of the O-polysaccharide isolated from Edwardsiella tarda PCM 1156 strain

  摘要：

  A convergent strategy has been developed for the synthesis of the tetrasaccharide repeating unit of the O-antigen from Edwardsiella tarda PCM 1156. Sequential glycosylations of a series of rationally protected monosaccharide intermediates were achieved either by the activation of thioglycosides using N-iodosuccinimide (NIS) in conjunction with H2SO4-silica or by activation of trichloroacetimidate by H2SO4-silica only. All glycosylation reactions resulted in the formation of the desired linkage with absolute stereoselectivity and yielded the required derivatives in good to excellent yields. Both azido and phthalimido groups have been used as the precursor of the desired acetamido group depending on the requirement of 1,2-cis- or 1,2-trans-glycosidic linkage. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.08.004
• 作为产物：
  描述：

  p-tolyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside 在 盐酸 、 camphor-10-sulfonic acid 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 26.5h， 生成 p-tolyl 4-O-benzoyl-2-O-benzyl-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of a Sulfated Tetrasaccharide Corresponding to a Rare Sequence in the Galactofucan Isolated from Sargassum polycystum

  摘要：

  The first chemical synthesis of a highly sulfated tetrasaccharide 1, as the rare sequence in the galactofucan isolated from the brown alga Sargassum polycystum, was achieved in a convergent and stereoselective manner. The key features of the synthetic strategy include construction of multiple contiguous 1,2-cis glycosidic bonds and [2 + 2] assembly based on the rationally developed D-galactose building block 6. The synthesized oligosaccharides were fully characterized using a combination of coupled-HSQC and other 2D NMR techniques.

  DOI：

  10.1021/jo500503r

文献信息

• Stereoselective Synthesis of a Sulfated Tetrasaccharide Corresponding to a Rare Sequence in the Galactofucan Isolated from <i>Sargassum polycystum</i>
  作者：Jun Zhou、Liping Yang、Wenhao Hu

  DOI：10.1021/jo500503r

  日期：2014.5.16

  The first chemical synthesis of a highly sulfated tetrasaccharide 1, as the rare sequence in the galactofucan isolated from the brown alga Sargassum polycystum, was achieved in a convergent and stereoselective manner. The key features of the synthetic strategy include construction of multiple contiguous 1,2-cis glycosidic bonds and [2 + 2] assembly based on the rationally developed D-galactose building block 6. The synthesized oligosaccharides were fully characterized using a combination of coupled-HSQC and other 2D NMR techniques.
• Concise synthesis of the tetrasaccharide repeating unit of the O-polysaccharide isolated from Edwardsiella tarda PCM 1156 strain
  作者：Rituparna Das、Mukul Mahanti、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2014.08.004

  日期：2014.11

  A convergent strategy has been developed for the synthesis of the tetrasaccharide repeating unit of the O-antigen from Edwardsiella tarda PCM 1156. Sequential glycosylations of a series of rationally protected monosaccharide intermediates were achieved either by the activation of thioglycosides using N-iodosuccinimide (NIS) in conjunction with H2SO4-silica or by activation of trichloroacetimidate by H2SO4-silica only. All glycosylation reactions resulted in the formation of the desired linkage with absolute stereoselectivity and yielded the required derivatives in good to excellent yields. Both azido and phthalimido groups have been used as the precursor of the desired acetamido group depending on the requirement of 1,2-cis- or 1,2-trans-glycosidic linkage. (C) 2014 Elsevier Ltd. All rights reserved.