(4S,5R)-3-(tert-butoxycarbonyl)-4-carboxy-5-methyl-1,3-oxazolidine | 161979-36-8

• 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: (4S,5R)-3-(tert-butoxycarbonyl)-4-carboxy-5-methyl-1,3-oxazolidine
• 英文别名: (4S,5R)-N-t-butoxycarbonyl-5-methyl-1,3-oxazolidine-4-carboxylic acid；(4S,5R)-5-methyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidine-4-carboxylic acid
• CAS: 161979-36-8
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: IFNULYQZWRMFCP-RQJHMYQMSA-N

物化性质

• 沸点：
  358.6±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (4S,5R)-3-(tert-butoxycarbonyl)-4-carboxy-5-methyl-1,3-oxazolidine 在 盐酸 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 作用下， 以 乙酸乙酯 为溶剂， 生成 (4S,5R)-5-methyl-N-(p-tolyl)oxazolidine-4-carboxamide
  参考文献：
  名称：

  Synthesis and in vitro antibacterial activity of oxazolidine LBM-415 analogs as peptide deformylase inhibitors

  摘要：

  The drug resistant bacteria pose a severe threat to human health. The increasing resistance of those pathogens to traditional antibacterial therapy renders the identification of new antibacterial agents with novel antibacterial mechanisms an urgent need. In this study, a series of (2S)-N-substituted-1-[(formyhydroxyamino) methyl]-1-oxohexyl]-2-oxazolidinecarboxamides were designed, synthesized and evaluated for in vitro antibacterial activity. Most of these compounds displayed good activities against Gram-positive organisms comparable to reference agent LBM-415. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.097
• 作为产物：
  描述：

  碳酸二叔丁酯 、 (4S,5R)-5-methyl-oxazolidine-4-carboxylic acid 在 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 (4S,5R)-3-(tert-butoxycarbonyl)-4-carboxy-5-methyl-1,3-oxazolidine
  参考文献：
  名称：

  含有杂原子的手性配体：13.。旋光的4-（2'-吡啶基）-1,3-恶唑烷：一种改进的2-（2'-吡啶基）-2-氨基醇的合成

  摘要：

  提出了通过1，3-恶唑烷衍生物以对映体纯形式改进的2-（2'-吡啶基）-2-氨基醇1a和1b的合成。还报道了一些用于裂解恶唑烷环和去除N -Boc保护基的有效和选择性的方法。

  DOI：

  10.1016/s0040-4020(01)89356-x

文献信息

• Highly Efficient Small Organic Molecules for Enantioselective Direct Aldol Reaction in Organic and Aqueous Media
  作者：Monika Raj Vishnumaya、Vinod K. Singh

  DOI：10.1021/jo900548f

  日期：2009.6.5

  A series of highly efficient organocatalysts have been derived from naturally available amino acids for carrying out enantioselective direct aldol reaction in both organic and aqueous medium. The aldol products were obtained in high diastereoselectivities (up to 99:1) and enantioselectivities (up to >99% ee) for a broader range of substrates using 1 mol % of a catalyst. The results demonstrate that

  已经从天然可用的氨基酸衍生出了一系列高效的有机催化剂，用于在有机和水性介质中进行对映选择性的直接羟醛反应。使用1 mol％的催化剂，可以在更大范围的底物上以高非对映选择性（最高99：1）和对映选择性（最高> 99％ee）获得醛醇产物。结果表明，有机催化剂的结构特征对于在水性介质中获得高光学纯度的醛醇加合物具有至关重要的作用。此外，已经说明了水在增加反应速率和对映选择性中的作用。而且，醛醇缩合产物已被用于手性氨基醇的合成中，手性氨基醇用作建立复杂的天然产物的有用的中间体。
• Optically active 4-oxaroline derivatives: New useful chiral synthons derived from serine and threonine
  作者：Massimo Falorni、Sandra Conti、Giampaolo Giacomelli、Sergio Cossu、Francesco Soccolini

  DOI：10.1016/0957-4166(94)00386-p

  日期：1995.1

  3-oxazolidine (4-oxaproline) derivatives starting from serine and threonine is described which avoids the use of toxic solvents or reagents. Elaboration of these compounds allows significant improvement in the handling of serine and threonine during the multigram preparation of oligopeptide structures and affords versatile chiral building blocks for the organic synthesis.

  描述了一种非常简单的从丝氨酸和苏氨酸开始制备手性旋光性N-保护的4-羧基-1,3-恶唑烷（4-氧杂脯氨酸）衍生物的方法，该方法避免了使用有毒溶剂或试剂。这些化合物的精制可以在多肽寡糖结构制备过程中显着改善丝氨酸和苏氨酸的处理，并为有机合成提供了通用的手性结构单元。
• HIV PROTEASE INHIBITORS, COMPOSITIONS CONTAINING THE SAME, THEIR PHARMACEUTICAL USES, MATERIALS FOR THEIR SYNTHESIS
  申请人：Kucera John David

  公开号：US20070066664A1

  公开（公告）日：2007-03-22

  Compounds of the formula: where the formula variables are as defined herein, are disclosed that advantageously inhibit or block the biological activity of the HIV protease. These compounds, as well as pharmaceutical compositions containing these compounds, are useful for treating patients or hosts infected with the HIV virus. Intermediates and synthetic methods for preparing such compounds are also described.

  本文披露了以下公式的化合物：其中公式变量如本文所定义，有利地抑制或阻断HIV蛋白酶的生物活性。这些化合物以及含有这些化合物的药物组合物，对于治疗感染HIV病毒的患者或宿主非常有用。还描述了制备这些化合物的中间体和合成方法。
• HIV protease inhibitors, compositions containing the same, their pharmaceutical uses and materials for their synthesis
  申请人：Canan Koch S. Stacie

  公开号：US20070021354A1

  公开（公告）日：2007-01-25

  Compounds of the formula: where the formula variables are as defined herein, are disclosed that advantageously inhibit or block the biological activity of the HIV protease. These compounds, as well as pharmaceutical compositions containing these compounds, are useful for treating patients or hosts infected with the HIV virus. Intermediates and synthetic methods for preparing such compounds are also described.

  公式为：其中公式变量如本文所定义，披露了有利地抑制或阻断HIV蛋白酶的生物活性的化合物。这些化合物以及含有这些化合物的药物组合物，对于治疗感染HIV病毒的患者或宿主是有用的。还描述了制备这些化合物的中间体和合成方法。
• NOVEL TRIPEPTIDE COMPOUNDS AND ANTI-AIDS DRUGS
  申请人：JAPAN ENERGY CORPORATION

  公开号：EP0900566A1

  公开（公告）日：1999-03-10

  A novel tripeptide compound represented by the following general formula (I) exhibiting superior HIV protease inhibition activity, and an anti-AIDS medicine comprising this compound as an effective component and a pharmaceutically acceptable salt thereof. (R)-N-(2-methylbenzyl)-3-(2S,3S)-3-[N-(2-chromonecarbonyl)-L-asparaginyl]amino-2-hydroxy-4-phenylbutanoyl}-5,5-dimethyl-1,3-thiazolidine-4-carboxamide can be given as a typical example of this compound.

  一种由以下通式(I)代表的新型三肽化合物，具有优异的抑制HIV蛋白酶活性，以及一种以该化合物为有效成分的抗艾滋病药物及其药学上可接受的盐。 (R)-N-(2-甲基苄基)-3-(2S,3S)-3-[N-(2-铬羰基)-L-天冬酰胺基]氨基-2-羟基-4-苯基丁酰基}-5,5-二甲基-1,3-噻唑烷-4-甲酰胺可作为该化合物的典型实例。