p-Tolyl 2,3-di-O-benzyl-1-thio-β-L-fucopyranoside | 1607433-64-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-Tolyl 2,3-di-O-benzyl-1-thio-β-L-fucopyranoside
• 英文别名: (2S,3R,4R,5S,6R)-2-methyl-6-(4-methylphenyl)sulfanyl-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 1607433-64-6
• 化学式: C₂₇H₃₀O₄S
• 分子量: 450.599
• InChiKey: NIRMOLYRVCSHLG-RBGCBHJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  p-Tolyl 2,3-di-O-benzyl-1-thio-β-L-fucopyranoside 、 氯乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 以89%的产率得到p-tolyl 2,3-di-O-benzyl-4-O-chloroacetyl-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Chemical synthesis of a tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1

  摘要：

  Chemical synthesis of the tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1 is reported. The stereoselective glycosylations were achieved by activation of the thioglycoside donors using N-iodosuccinimide in the presence of La(OTf)(3) varying temperature per the need of 1,2-cis or 1,2-trans glycosylations. The target tetrasaccharide is reported in the form of its p-methoxyphenyl glycoside that can be cleaved selectively from the per-O-acetylated derivative allowing further glycoconjugate formation using trichloroacetimidate chemistry. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.018
• 作为产物：
  描述：

  p-tolyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside 在 sodium methylate 、 sodium hydride 、 二正丁基氧化锡 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 61.5h， 生成 p-Tolyl 2,3-di-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.
• Chemical synthesis of a tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1
  作者：Darshita Budhadev、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2014.05.018

  日期：2014.7

  Chemical synthesis of the tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1 is reported. The stereoselective glycosylations were achieved by activation of the thioglycoside donors using N-iodosuccinimide in the presence of La(OTf)(3) varying temperature per the need of 1,2-cis or 1,2-trans glycosylations. The target tetrasaccharide is reported in the form of its p-methoxyphenyl glycoside that can be cleaved selectively from the per-O-acetylated derivative allowing further glycoconjugate formation using trichloroacetimidate chemistry. (C) 2014 Elsevier Ltd. All rights reserved.