[4(R)-2-oxo-1,3-oxazolidin-4-ylmethyl]triphenylphosphonium iodide | 142319-37-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [4(R)-2-oxo-1,3-oxazolidin-4-ylmethyl]triphenylphosphonium iodide
• 英文别名: [(4R)-2-oxo-1,3-oxazolidin-4-yl]methyl-triphenylphosphanium;iodide
• CAS: 142319-37-7
• 化学式: C₂₂H₂₁NO₂P*I
• 分子量: 489.293
• InChiKey: IOJSWCZYCHHOEG-GMUIIQOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-二氟苯甲醛 、 [4(R)-2-oxo-1,3-oxazolidin-4-ylmethyl]triphenylphosphonium iodide 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以75%的产率得到(4S)-4-[(E)-2-(2,4-difluorophenyl)ethenyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  从手性氮丙啶新型立体选择性合成功能化的恶唑烷酮。

  摘要：

  对映体纯的N-（R）-α-甲基苄基-4（R）-（氯甲基）恶唑烷酮（4R）-5a-k一步合成，并从各种氮丙啶-2-甲醇（S）-2a-k中高收率通过光气进行分子内环化。氮上的α-甲基苄基取代基很容易裂解，得到4-（氯甲基）恶唑烷酮（R）-7a和（S）-7a的两种对映体。（R）-7a用于有效合成（L）-高苯丙氨醇类似物（S）-12a-j。我们还应用了相同的方法，以高收率制备了在C-4处含有杂原子取代的烷基的恶唑烷酮9a-c。

  DOI：

  10.1021/jo025545l
• 作为产物：
  描述：

  三苯基膦 、 4(R)-(chloromethyl)oxazolidin-2-one 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以95%的产率得到[4(R)-2-oxo-1,3-oxazolidin-4-ylmethyl]triphenylphosphonium iodide
  参考文献：
  名称：

  从手性氮丙啶新型立体选择性合成功能化的恶唑烷酮。

  摘要：

  对映体纯的N-（R）-α-甲基苄基-4（R）-（氯甲基）恶唑烷酮（4R）-5a-k一步合成，并从各种氮丙啶-2-甲醇（S）-2a-k中高收率通过光气进行分子内环化。氮上的α-甲基苄基取代基很容易裂解，得到4-（氯甲基）恶唑烷酮（R）-7a和（S）-7a的两种对映体。（R）-7a用于有效合成（L）-高苯丙氨醇类似物（S）-12a-j。我们还应用了相同的方法，以高收率制备了在C-4处含有杂原子取代的烷基的恶唑烷酮9a-c。

  DOI：

  10.1021/jo025545l

文献信息

• The metathesis reaction for side chain construction in carbocyclic sinefungin analogue synthesis
  作者：Qi Chen、Chong Liu、Tetyana S. Shulyak、Stewart W. Schneller

  DOI：10.1016/j.tet.2013.12.030

  日期：2014.1

  The naturally occurring nucleoside sinefungin has found considerable use in biological investigations. More extensive sinefungin studies have been limited because few analogues have been reported due to the synthetic challenges associated with such studies. Reported herein are preparative ways to two carbocyclic sinefungin analogues: 6'-deaminocarbocyclic sinefungin and (S)-6'-hydroxy-6'-deamino-carbocyclic sinefimgin. The synthetic routes were made efficient and practical by the application of two metathesis reactions employing second generation Grubbs catalyst. (C) 2013 Elsevier Ltd. All rights reserved.
• Enantiospecific Synthesis of (−)-Slaframine and Related Hydroxylated Indolizidines. Utilization of a Nucleophilic Alaninol Synthon Derived from Serine¹
  作者：Mukund P. Sibi、James W. Christensen

  DOI：10.1021/jo9908546

  日期：1999.8.1

  A general methodology for the synthesis of indolizidine alkaloids delta-coniceine (12), 1-hydroxyindolizidine (20), desacetoxy slaframine (24), slaframine (34), and an analogue (37) has been developed. This convergent approach utilizes the available chirality in proline and serine and is conceptually different from other approaches. A highly stereoselective coupling of the prolinals with a nucleophilic alaninol synthon provides the precursors for the key cyclization. A novel thermolytic annulation of an oxazolidinone is the key step in the formation of the six-membered piperidine ring. Further elaboration provides the target natural products 24, 34, and 37 in good overall yields.
• Synthesis of β-<scp>d</scp>-Galactosyl Ceramide Methylene Isostere
  作者：Alessandro Dondoni、Daniela Perrone、Elisa Turturici

  DOI：10.1021/jo990398l

  日期：1999.7.1

  The methylene isostere of the glycosphingolipid beta-D-galactosyl N-palmitoyl C-18 ceramide has been synthesized by a linear reaction sequence starting from a beta-linked D-galactopyranosyl aldehyde. First, this sugar aldehyde was converted into a methylenephosphorane which in turn was coupled with N-Boc serinal acetonide. The double bond of the resulting olefin was reduced and the oxazolidine ring was cleaved and oxidized to give a C-glycosyl N-Boc alpha-amino butanal (three-carbon chain elongation). Then, an additional C-15 carbon chain was installed by addition of lithium 1-pentadecyne to the above glycosyl amino aldehyde. The syn/anti ratio (70:30) of the resulting mixture of amino alcohols was reversed (5:95) by an oxidation-reduction sequence to achieve the same stereochemistry as in the hydrophilic head of D-erythro-sphingosines. The major product was subjected to the reduction of the triple bond with LiAlH4 to give the olefin with E geometry. Finally the N-amide group was installed by reaction with palmitoyl chloride and the O-benzyl protective groups of the sugar moiety were removed by treatment with lithium in liquid NH3-THF. The final product was characterized as the O-acetyl derivative.
• A novel thermolytic annulation of an oxazolidinone: an enantiospecific synthesis of (-)-slaframine
  作者：Mukund P. Sibi、James W. Christensen、Biqin Li、Paul A. Renhowe

  DOI：10.1021/jo00042a002

  日期：1992.7

  Optically pure beta-aminopiperidines can be prepared in high yields through a thermolytic annulation sequence involving ring opening of an oxazolidinone.
• Versatile synthesis of (+)-deoxypyridinoline, a biochemical marker for diagnosis of osteoporosis
  作者：Maciej Adamczyk、Srinivasa Rao Akireddy、Rajarathnam E. Reddy

  DOI：10.1016/s0957-4166(99)00329-8

  日期：1999.8

  A versatile chiral synthesis of the bone collagen cross-link, (+)-deoxypyridinoline (Dpd, 1) was described starting from a 3-hydroxypyridine derivative (2) via sequential introduction of three amino acid chains followed by hydrolysis. The key synthon 2, was prepared from vitamin B-6 (6). (C) 1999 Published by Elsevier Science Ltd. All rights reserved.