4,6-di-O-acetyl-2-O-allyl-3-O-benzyl-α-D-glucopyranosyl chloride | 189144-59-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,6-di-O-acetyl-2-O-allyl-3-O-benzyl-α-D-glucopyranosyl chloride
• 英文别名: [(2R,3R,4S,5R,6R)-3-acetyloxy-6-chloro-4-phenylmethoxy-5-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 189144-59-0
• 化学式: C₂₀H₂₅ClO₇
• 分子量: 412.867
• InChiKey: JDSUJLVYVLFHDX-OBKDMQGPSA-N

物化性质

• 沸点：
  499.4±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,6-di-O-acetyl-2-O-allyl-3-O-benzyl-α-D-glucopyranosyl chloride 在 palladium on activated charcoal 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 sodium acetate 、 silver trifluoromethanesulfonate 、 一水合肼 、 溶剂黄146 、 palladium dichloride 作用下， 以 甲醇 、 乙醇 、 水 、 溶剂黄146 为溶剂， 23.0 ℃ 、1.38 MPa 条件下， 反应 121.33h， 生成 6-[(2S,3R,4S,5S,6R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanehydrazide
  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：

  methyl 2-O-allyl-3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 在 吡啶 、 zinc chloride diethyl ether 、 1,1-二氯甲醚 、 硫酸 、 水 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 2.8h， 生成 4,6-di-O-acetyl-2-O-allyl-3-O-benzyl-α-D-glucopyranosyl chloride
  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