p-Tolyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside | 1607433-62-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-Tolyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside
• 英文别名: (3aR,4S,6R,7S,7aR)-2,2,4-trimethyl-6-(4-methylphenyl)sulfanyl-7-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
• CAS: 1607433-62-4
• 化学式: C₂₃H₂₈O₄S
• 分子量: 400.539
• InChiKey: LKZJLVQADPTSSV-LOONRQLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  p-Tolyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 在 溶剂黄146 作用下， 反应 2.0h， 以91%的产率得到p-tolyl 2-O-benzyl-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 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 21.5h， 生成 p-Tolyl 2-O-benzyl-3,4-O-isopropylidene-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

• Chemical synthesis of the tetrasaccharide repeating unit of the O-polysaccharide isolated from Azospirillum brasilense SR80
  作者：Vikramjit Sarkar、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2015.01.008

  日期：2015.4

  A linear strategy has been developed for the synthesis of the tetrasaccharide repeating unit of the O-polysaccharide from Azospirillum brasilense SR80. Stepwise glycosylation of the rationally protected thioglycoside donors activated by NIS in the presence of La(OTf)(3) furnished the target tetrasaccharide. The glycosylation reactions resulted in the formation of the desired linkage with absolute stereo-selectivity and afforded the required derivatives in good to excellent yields. The phthalimido group has been used as the precursor of the desired acetamido group to meet the requirement of 1,2-trans glycosidic linkage. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of the tetrasaccharide repeating unit of the O -glycan from the polar flagellum flagellin of Azospirillum brasilense Sp7
  作者：Kumar Bhaskar Pal、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2014.06.019

  日期：2014.12

  Chemical synthesis of the tetrasaccharide repeating unit of the O-glycan from the polar flagellum flagellin of Azospirillum brasilense Sp7 in the form of its p-methoxyphenyl glycoside is reported. The required glycosidic linkages have been accomplished by activation of thioglycosides with N-iodosuccinimide in the presence of H2SO4-silica. H2SO4-silica was found to be an effective alternative to the classical acid promoters like TfOH or TMSOTf and it can lead to the formation of both 1,2-cis and 1,2-trans glycosidic linkages depending on the protecting group manipulation and control of the reaction condition. (C) 2014 Elsevier Ltd. All rights reserved.