tert-butyl (Z)-2,2-dimethyl-4-(1'-butenyl)-3-oxazolidinecarboxylate | 140169-92-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: tert-butyl (Z)-2,2-dimethyl-4-(1'-butenyl)-3-oxazolidinecarboxylate
• CAS: 140169-92-2
• 化学式: C₁₄H₂₅NO₃
• 分子量: 255.357
• InChiKey: WAEROZPRSAMFIU-TYBABMIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (Z)-2,2-dimethyl-4-(1'-butenyl)-3-oxazolidinecarboxylate 在 咪唑 、 盐酸 、 N-羟基丁二酰亚胺 、 四氧化锇 、 N-甲基吲哚酮 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 叔丁醇 为溶剂， 反应 9.08h， 生成 Tetracosanoic acid [(1S,2S,3R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydroxy-pentyl]-amide
  参考文献：
  名称：

  Effects of Lipid Chain Lengths in α-Galactosylceramides on Cytokine Release by Natural Killer T Cells

  摘要：

  Glycolipid presentation by CD1 proteins has emerged as an important aspect of antigen recognition, and presentation of alpha-glycosylceramides by CD1d to natural killer T cells has become a central focus in understanding how glycolipid presentation can influence immune responses. An alpha-galactosylceramide containing relatively long lipid chains has been the subject of intense study because, when presented by CD1d to natural killer T cells, it stimulates the release of both proinflammatory and immunomodulatory cytokines. Using an efficient synthesis of alpha-galactosylceramides, we have prepared a series of glycolipids in which the lipid chain lengths have been incrementally varied. The responses of natural killer T cells to these glycolipids have been determined, and we have found that truncation of the phytosphingosine lipid chain increases the relative amounts of immunomodulatory cytokines released. In similar fashion, the length of the acyl chain in alpha-galactosylceramides influences cytokine release profiles.

  DOI：

  10.1021/ja045385q
• 作为产物：
  描述：

  3-反-溴碳-2,2'-二甲基氧酸酯 、 三苯基丙基溴化 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 tert-butyl (Z)-2,2-dimethyl-4-(1'-butenyl)-3-oxazolidinecarboxylate
  参考文献：
  名称：

  Effects of Lipid Chain Lengths in α-Galactosylceramides on Cytokine Release by Natural Killer T Cells

  摘要：

  Glycolipid presentation by CD1 proteins has emerged as an important aspect of antigen recognition, and presentation of alpha-glycosylceramides by CD1d to natural killer T cells has become a central focus in understanding how glycolipid presentation can influence immune responses. An alpha-galactosylceramide containing relatively long lipid chains has been the subject of intense study because, when presented by CD1d to natural killer T cells, it stimulates the release of both proinflammatory and immunomodulatory cytokines. Using an efficient synthesis of alpha-galactosylceramides, we have prepared a series of glycolipids in which the lipid chain lengths have been incrementally varied. The responses of natural killer T cells to these glycolipids have been determined, and we have found that truncation of the phytosphingosine lipid chain increases the relative amounts of immunomodulatory cytokines released. In similar fashion, the length of the acyl chain in alpha-galactosylceramides influences cytokine release profiles.

  DOI：

  10.1021/ja045385q

文献信息

• Synthesis of asymmetric (E)-α-–phenyl(ethyl)cyclopropylλycines from serine by diastereoselective dibromocylopropanation
  作者：Ma Pilar de Frutos、Ma Dolores Fernández、E. Fernández-Alvarez、Manuel Bernabé*

  DOI：10.1016/s0040-4020(01)88208-9

  日期：1992.1

  An asymmetric synthesis of (E)-α-(2-phenylcyclopropyl)glycines and also of a homolog of allocoronamic acid, namely (E)-α-(2-ethylcyclopropyl)glycine, is reported. The key step is the dibromocyclopropanation of tert-butyl (E, 4R)- or (E, 4)-2,2-dimethyl-4-(2′-phenylvinyl)- and -(2′-ethylvinyl)-3-oxazolidinecarboxylates, easily prepared from L- or D- serine. This reaction gives good diastereomeric ratios

  报道了（E）-α-（2-苯基环丙基）甘氨酸的不对称合成，以及正膦酸的同系物，即（E）-α-（2-乙基环丙基）甘氨酸的不对称合成。关键步骤是（E，4R）-或（E，4）-2,2-二甲基-4-（2'-苯基乙烯基）-和-（2'-乙基乙烯基）-3-恶唑烷羧酸酯的叔丁基二溴环丙烷化，可轻松从L-或D-丝氨酸制备。该反应给出了良好的非对映异构体比例的二溴环丙烷。分三步将主要化合物转化为相应的环丙基氨基酸。