N-Boc-N-methyl-O-(3-chloropropyl)-hydroxylamine | 1152438-41-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-Boc-N-methyl-O-(3-chloropropyl)-hydroxylamine
• 英文别名: 3-chloro-1-(O-[N-Boc,N-methyl]amino)hydroxypropane；Carbamic acid, N-(3-chloropropoxy)-N-methyl-, 1,1-dimethylethyl ester；tert-butyl N-(3-chloropropoxy)-N-methylcarbamate
• CAS: 1152438-41-9
• 化学式: C₉H₁₈ClNO₃
• 分子量: 223.7
• InChiKey: RMXQFSYBYFOYFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-甲基苯磺酰基-3-氯-1-丙醇 、 N-羟基-N-甲基氨基甲酸叔丁酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以61%的产率得到N-Boc-N-methyl-O-(3-chloropropyl)-hydroxylamine
  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

文献信息

• Chemoselective and Microwave-Assisted Synthesis of Glycopeptoids
  作者：Jiwon Seo、Nairie Michaelian、Shawn C. Owens、Scott T. Dashner、Amanda J. Wong、Annelise E. Barron、Michael R. Carrasco

  DOI：10.1021/ol9021468

  日期：2009.11.19

  The chemoselective glycosylation of N-alkylaminooxy side chains with unprotected reducing sugars has proven useful for the synthesis of glycopeptides. Herein, we extend the N-alkylaminooxy strategy to the synthesis of glycopeptoids. A N-methylaminooxy submonomer was efficiently synthesized and incorporated into peptoids. Glycosylation of the peptoids proceeded chemoselectively and site-specifically

  N-烷基氨基氧基侧链与未保护的还原糖的化学选择性糖基化已被证明可用于合成糖肽。在这里，我们将N-烷基氨基氧基策略扩展到糖肽类的合成。甲Ñ -methylaminooxy亚单体被有效地合成，并纳入拟肽。类肽的糖基化在N-甲基氨基氧基部分进行化学选择性和位点特异性。采用微波辐射显着增加了糖基化程度并缩短了反应时间。