methyl 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]oxyhexanoate | 189144-73-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 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]oxyhexanoate
• CAS: 189144-73-8
• 化学式: C₂₅H₄₄O₁₈
• 分子量: 632.614
• InChiKey: LOGOMPBEAFEGAI-WUDKOHAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  284
• 氢给体数：
  10
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  methyl 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]oxyhexanoate 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以72%的产率得到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：

  6-羟基己酸甲酯 在 palladium on activated charcoal 1-己烯 、 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 sodium acetate 、 silver trifluoromethanesulfonate 、 silver perchlorate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 silver carbonate 、 palladium dichloride 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 23.0 ℃ 、2.07 MPa 条件下， 反应 159.67h， 生成 methyl 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]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

文献信息

• Chemical approaches to bacterial vaccines. synthesis of mycobacterial oligosaccharide-protein conjugates for use as serodiagnostics and immunogens
  作者：Eric P Dubois、John B Robbins、Vince Pozsgay

  DOI：10.1016/0960-894x(96)00235-1

  日期：1996.6

  Di- to penta-saccharide fragments (2-5) of Polysaccharide II (PS-II) of Mycobacterium tuberculosis were synthesized in spacer-linked form in a stepwise fashion using a new glycosyl donor featuring a trans-fused isopropylidene diol-protecting group. Covalent attachment of the oligosaccharides to proteins provides semi-synthetic antigens and immunogens which are being used to probe the role of PS-II as a possible mycobacterial antigen.
• Synthesis of Kojidextrins and Their Protein Conjugates. Incidence of Steric Mismatch in Oligosaccharide Synthesis
  作者：Vince Pozsgay、Eric P. Dubois、Lewis Pannell

  DOI：10.1021/jo962300y

  日期：1997.5.1

  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.