phenyl 4,6-di-O-acetyl-2-O-allyl-3-O-benzyl-1-thio-β-D-glucopyranoside | 189144-58-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4,6-di-O-acetyl-2-O-allyl-3-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: allyl(-2)[Bn(-3)]Glc4Ac6Ac(b)-SPh；[(2R,3R,4S,5R,6S)-3-acetyloxy-4-phenylmethoxy-6-phenylsulfanyl-5-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 189144-58-9
• 化学式: C₂₆H₃₀O₇S
• 分子量: 486.586
• InChiKey: BITUCKRLHXPFIG-RTJMFUJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-di-O-acetyl-2-O-allyl-3-O-benzyl-1-thio-β-D-glucopyranoside 在 草酰氯 、 zinc chloride diethyl ether 、 1,1-二氯甲醚 、 4 A molecular sieve 、 sodium acetate 、 silver perchlorate 、 silver carbonate 、 三氟乙酸 、 palladium dichloride 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 110.0h， 生成 methyl 6-[(2S,3R,4S,5R,6R)-4,5-diacetyloxy-3-[(2R,3R,4S,5R,6R)-5-acetyloxy-3-[(2R,3R,4R,5R,6R)-5-acetyloxy-6-(acetyloxymethyl)-3-hydroxy-4-phenylmethoxyoxan-2-yl]oxy-6-(acetyloxymethyl)-4-phenylmethoxyoxan-2-yl]oxy-6-(acetyloxymethyl)oxan-2-yl]oxyhexanoate
  参考文献：
  名称：

  Synthesis of Kojidextrins and Their Protein Conjugates. Incidence of Steric Mismatch in Oligosaccharide Synthesis

  摘要：

  Kojidextrins are biologically important oligosaccharides that are involved in many physiological processes including protein glycosylation and bacterial growth. As part of our project to explore the role kojidextrins may play in bacterial pathogenesis, here we report Synthetic routes to kojibiose (54), -triose (58), -tetraose (64), and -pentaose (69) equipped with alpha-linked (hydrazinocarbonyl)-pentyl aglycon, using linear and convergent strategies. In the search for a rapid convergent strategy for the construction of extended kojidextrins, four kojibiose donors (1-4) were synthesized that contain acyl- and ether-type protecting groups in various ratios. These were tested to probe the influence of diverse protecting group assemblies on their glycosyl donor ability. Attempted condensation of these donors with kojitriose and -tetraose accepters failed to give the desired products apparently because of steric mismatch between the donor and the acceptor moieties. A one-pot procedure was developed for the covalent attachment of the synthetic saccharides through their hydrazido group to human serum albumin (HSA) using Tietze's squarate method to give neoglycoproteins containing up to 28 saccharide units per HSA.

  DOI：

  10.1021/jo962300y
• 作为产物：
  描述：

  phenyl 2-O-allyl-3-O-benzyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside 在 吡啶 、 tetrafluoroboric acid 作用下， 以 甲醇 、 乙醚 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 phenyl 4,6-di-O-acetyl-2-O-allyl-3-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Kojidextrins and Their Protein Conjugates. Incidence of Steric Mismatch in Oligosaccharide Synthesis

  摘要：

  Kojidextrins are biologically important oligosaccharides that are involved in many physiological processes including protein glycosylation and bacterial growth. As part of our project to explore the role kojidextrins may play in bacterial pathogenesis, here we report Synthetic routes to kojibiose (54), -triose (58), -tetraose (64), and -pentaose (69) equipped with alpha-linked (hydrazinocarbonyl)-pentyl aglycon, using linear and convergent strategies. In the search for a rapid convergent strategy for the construction of extended kojidextrins, four kojibiose donors (1-4) were synthesized that contain acyl- and ether-type protecting groups in various ratios. These were tested to probe the influence of diverse protecting group assemblies on their glycosyl donor ability. Attempted condensation of these donors with kojitriose and -tetraose accepters failed to give the desired products apparently because of steric mismatch between the donor and the acceptor moieties. A one-pot procedure was developed for the covalent attachment of the synthetic saccharides through their hydrazido group to human serum albumin (HSA) using Tietze's squarate method to give neoglycoproteins containing up to 28 saccharide units per HSA.

  DOI：

  10.1021/jo962300y