tert-butyl (4R,1'R)-2,2-dimethyl-4-(1'-hydroxyhexadec-2'-ynyl)oxazolidione-3-carboxylate | 928302-04-9

• 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'R)-2,2-dimethyl-4-(1'-hydroxyhexadec-2'-ynyl)oxazolidione-3-carboxylate
• 英文别名: tert-butyl (4R)-4-[(1R)-1-hydroxyhexadec-2-ynyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 928302-04-9
• 化学式: C₂₆H₄₇NO₄
• 分子量: 437.663
• InChiKey: JKAJAOBVDVKBPE-DHIUTWEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  31.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (4R,1'R)-2,2-dimethyl-4-(1'-hydroxyhexadec-2'-ynyl)oxazolidione-3-carboxylate 在 甲醇 、 Amberlyst 15 、 红铝 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 72.0h， 生成 2-(N-tert-butoxycarbonyl)-(2R,3R,4E)-4-octadene-1,3-diol
  参考文献：
  名称：

  Synthesis of fluorescent lactosylceramide stereoisomers

  摘要：

  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.

  DOI：

  10.1016/j.chemphyslip.2006.03.001
• 作为产物：
  描述：

  (R)-(+)-3-叔丁氧羰基-2,2-二甲基-4-噁唑烷羧酸甲 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 5.0h， 生成 tert-butyl (4R,1'R)-2,2-dimethyl-4-(1'-hydroxyhexadec-2'-ynyl)oxazolidione-3-carboxylate
  参考文献：
  名称：

  Synthesis of fluorescent lactosylceramide stereoisomers

  摘要：

  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.

  DOI：

  10.1016/j.chemphyslip.2006.03.001

文献信息

• First Total Synthesis of Symbioramide, a Novel Ca²⁺-ATPase Activator from<i>Symbiodinium</i>sp.
  作者：Masako Nakagawa、Jun Yoshida、Tohru Hino

  DOI：10.1246/cl.1990.1407

  日期：1990.8

  The first total synthesis of symbioramide (1) is described and simultaneously established the complete stereostructure of 1 to be (2S,3R,2′R,3′E)-N-(2′-hydroxy-3′-octadecenoyl)-dihydrosphingosine.

  描述了symbioramide (1) 的首次全合成，并同时确定了1的完整立体结构为(2S,3R,2′R,3′E)-N-(2′-羟基-3′-十八烯酰)-二氢鞘氨醇。
• 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：——