t-butyl 3,3'-disulfanediylbis(propane-3,1-diyl)bis(oxy)bis(methylcarbamate) | 1152438-42-0

• 分子结构分类: 有机化合物 - 有机硫化合物
• 英文名称: t-butyl 3,3'-disulfanediylbis(propane-3,1-diyl)bis(oxy)bis(methylcarbamate)
• CAS: 1152438-42-0
• 化学式: C₁₈H₃₆N₂O₆S₂
• 分子量: 440.626
• InChiKey: AIPBUXPIQSFUBU-UHFFFAOYSA-N

物化性质

• 沸点：
  514.4±35.0 °C(predicted)
• 密度：
  1.135±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  77.54
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  t-butyl 3,3'-disulfanediylbis(propane-3,1-diyl)bis(oxy)bis(methylcarbamate) 在 水 、 三氟乙酸 作用下， 反应 0.5h， 以78%的产率得到1,2-bis(N-methyl-O-propyl-hydroxylamine)disulfide
  参考文献：
  名称：

  Efficient synthesis and protein conjugation of β-(1→6)-d-N-acetylglucosamine oligosaccharides from the polysaccharide intercellular adhesin

  摘要：

  A wide variety of medically important biofilm forming bacteria produce similar polysaccharide intracellular adhesins (PIAs). The PIA structures consist of partially de-N-acetylated beta-(1 -> 6)-N-acetylglucosamine polymers. These exopolysaccharides are key components of the bacterial biofilm matrix. Here, we describe the efficient synthesis of PIA oligosaccharides using an acid reversion reaction of N-acetylglucosamine in HF pyridine. The PIA oligosaccharides produced by this reaction can be purified to homogeneity by size exclusion chromatography. Chemistry was developed to conjugate the PIA oligosaccharides to bovine serum albumin using a new heterobifunctional linker containing a thiol and an N-methylhydroxylamine functional group. These glycoconjugates may serve as useful precursors for the development of defined conjugate vaccines against PIA producing bacterial strains. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.12.021
• 作为产物：
  描述：

  N-Boc-N-methyl-O-(3-chloropropyl)-hydroxylamine 在 potassium thioacyanate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以79%的产率得到t-butyl 3,3'-disulfanediylbis(propane-3,1-diyl)bis(oxy)bis(methylcarbamate)
  参考文献：
  名称：

  Efficient synthesis and protein conjugation of β-(1→6)-d-N-acetylglucosamine oligosaccharides from the polysaccharide intercellular adhesin

  摘要：

  A wide variety of medically important biofilm forming bacteria produce similar polysaccharide intracellular adhesins (PIAs). The PIA structures consist of partially de-N-acetylated beta-(1 -> 6)-N-acetylglucosamine polymers. These exopolysaccharides are key components of the bacterial biofilm matrix. Here, we describe the efficient synthesis of PIA oligosaccharides using an acid reversion reaction of N-acetylglucosamine in HF pyridine. The PIA oligosaccharides produced by this reaction can be purified to homogeneity by size exclusion chromatography. Chemistry was developed to conjugate the PIA oligosaccharides to bovine serum albumin using a new heterobifunctional linker containing a thiol and an N-methylhydroxylamine functional group. These glycoconjugates may serve as useful precursors for the development of defined conjugate vaccines against PIA producing bacterial strains. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.12.021