tert-butyl (4R,1'S)-2,2-dimethyl-4-(1'-hydroxyhexadec-2'-ynyl)oxazolidione-3-carboxylate | 524939-19-3

• 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 (4R,1'S)-2,2-dimethyl-4-(1'-hydroxyhexadec-2'-ynyl)oxazolidione-3-carboxylate
• 英文别名: tert-butyl (4R)-4-[(1S)-1-hydroxyhexadec-2-ynyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 524939-19-3
• 化学式: C₂₆H₄₇NO₄
• 分子量: 437.663
• InChiKey: JKAJAOBVDVKBPE-PKTZIBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (4R,1'S)-2,2-dimethyl-4-(1'-hydroxyhexadec-2'-ynyl)oxazolidione-3-carboxylate 在 lithium 、 乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 L-赤式-鞘氨醇
  参考文献：
  名称：

  Synthesis of penaresidin derivatives and its biological activity

  摘要：

  A series of stereoisomers for the azetidine ring of penaresidin B was synthesized and their cytotoxic and antimicrobial activities were evaluated. Among six synthetic isomers 1-6, isomers 4 and 5 showed relatively potent cytotoxic activity against A549 (lung) and HT29 (colon) tumor cells as well as antibacterial activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.049
• 作为产物：
  描述：

  Boc-L-丝氨酸甲酯 在 正丁基锂 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl (4R,1'S)-2,2-dimethyl-4-(1'-hydroxyhexadec-2'-ynyl)oxazolidione-3-carboxylate
  参考文献：
  名称：

  Synthesis and immobilization of ceramide analogs on silica particles

  摘要：

  Ceramides are the major lipid components of the stratum corneum, the major permeability barrier of the skin. Here we report a chemical synthesis of ceramide analogs covalently bonded on the silica particles, that can be used to predict the skin permeability of chemicals via HPLC methods. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(97)10217-7

文献信息

• Synthesis of fluorescent lactosylceramide stereoisomers
  作者：Yidong Liu、Robert Bittman

  DOI：10.1016/j.chemphyslip.2006.03.001

  日期：2006.7

  The intracellular distribution of synthetic glycosphingolipids (GSLs) bearing a fluorophore can be monitored in living cells by fluorescence microscopy. We reported previously that variation in the length of the long-chain base and in the structure of the carbohydrate-containing polar head group of (2S,3R) (or D-erythro-)-beta-lactosylceramide (LacCer) did not alter the mechanism of endocytic uptake from the plasma membrane of various mammalian cell types [Singh, R.D., Puri, V., Valiyaveettil, J.T., Marks, D.L., Bittman, R., Pagano, R.E., 2003. Selective caveolin-l-dependent endocytosis of glycosphingolipids. Mol. Biol. Cell 14, 3254-3265]. To extend our examination of the molecular features in LacCer that are responsible for its uptake by the caveolar-requiring endocytic pathway, we have synthesized the three unnatural stereoisomers [(2R,3R)-, (2S,3S)-, and (2R,3S)] of dipyrromethene difluoride (BODIPY (TM))-LacCer. These analogues will be used to probe the role of stereochemistry in the long-chain base of LacCer in the mechanism of endocytic uptake. (c) 2006 Elsevier Ireland Ltd. All rights reserved.
• NIMKAR, SANJAY;MENALDINO, DAVID;MERRILL, ALFRED H.;LIOTTA, DENNIS, TETRAHEDRON LETT., 29,(1988) N 25, C. 3037-3040
  作者：NIMKAR, SANJAY、MENALDINO, DAVID、MERRILL, ALFRED H.、LIOTTA, DENNIS

  DOI：——

  日期：——
• Synthesis and immobilization of ceramide analogs on silica particles
  作者：Jianming Yin、Hanlan Liu、Charles Pidgeon

  DOI：10.1016/s0960-894x(97)10217-7

  日期：1998.1

  Ceramides are the major lipid components of the stratum corneum, the major permeability barrier of the skin. Here we report a chemical synthesis of ceramide analogs covalently bonded on the silica particles, that can be used to predict the skin permeability of chemicals via HPLC methods. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of penaresidin derivatives and its biological activity
  作者：Kengo Ohshita、Haruaki Ishiyama、Yohei Takahashi、Junji Ito、Yuzuru Mikami、Jun’ichi Kobayashi

  DOI：10.1016/j.bmc.2007.04.049

  日期：2007.7

  A series of stereoisomers for the azetidine ring of penaresidin B was synthesized and their cytotoxic and antimicrobial activities were evaluated. Among six synthetic isomers 1-6, isomers 4 and 5 showed relatively potent cytotoxic activity against A549 (lung) and HT29 (colon) tumor cells as well as antibacterial activity. (c) 2007 Elsevier Ltd. All rights reserved.