benzyl (4R)-4-(3-hydroxypropyl)-5-oxo-1,3-oxazolidine-3-carboxylate | 716349-66-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl (4R)-4-(3-hydroxypropyl)-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 716349-66-5
• 化学式: C₁₄H₁₇NO₅
• 分子量: 279.293
• InChiKey: LFILUXSYTPLDAP-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (4R)-4-(3-hydroxypropyl)-5-oxo-1,3-oxazolidine-3-carboxylate 在 palladium on activated charcoal 咪唑 、 4 A molecular sieve 、 氢气 、 碳酸氢钠 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 324.5h， 生成 methyl-(2R)-2-(buta-1,3-dienyl-isobutyrylamin)-5-(hydroxy)pentanoate
  参考文献：
  名称：

  Stereoselective synthesis of the cis-275B decahydroquinoline ring system

  摘要：

  The Diels-Alder precursor was constructed from readily available D-glutamic acid utilizing a series of functional group transformations. The stereocenter of the amino acid provided the desired stereochemistry at C2 and diastereoselectively directed the intramolecular Diels-Alder cyclization. This simultaneously generated the three remaining stereocenters and yielded a bicyclic intermediate with all four stereocenters of the target decahydroquinoline 275B. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.191
• 作为产物：
  描述：

  (4R)-4-(2-Carboxyethyl)-3-[(phenylmethoxy)carbonyl]oxazolidin-5-one 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 benzyl (4R)-4-(3-hydroxypropyl)-5-oxo-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Stereoselective synthesis of the cis-275B decahydroquinoline ring system

  摘要：

  The Diels-Alder precursor was constructed from readily available D-glutamic acid utilizing a series of functional group transformations. The stereocenter of the amino acid provided the desired stereochemistry at C2 and diastereoselectively directed the intramolecular Diels-Alder cyclization. This simultaneously generated the three remaining stereocenters and yielded a bicyclic intermediate with all four stereocenters of the target decahydroquinoline 275B. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.191

文献信息

• Stereoselective synthesis of the cis-275B decahydroquinoline ring system
  作者：Edith J. Banner、Edwin D. Stevens、Mark L. Trudell

  DOI：10.1016/j.tetlet.2004.03.191

  日期：2004.5

  The Diels-Alder precursor was constructed from readily available D-glutamic acid utilizing a series of functional group transformations. The stereocenter of the amino acid provided the desired stereochemistry at C2 and diastereoselectively directed the intramolecular Diels-Alder cyclization. This simultaneously generated the three remaining stereocenters and yielded a bicyclic intermediate with all four stereocenters of the target decahydroquinoline 275B. (C) 2004 Elsevier Ltd. All rights reserved.