(4S)-benzyl-(2S)-tert-butyl-5-oxooxazolidine-3-carboxylic acid allyl ester

• 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)-benzyl-(2S)-tert-butyl-5-oxooxazolidine-3-carboxylic acid allyl ester
• 英文别名: Allyl(2s,4s)-4-benzyl-2-tert-butyl-5-oxooxazolidine-3-carboxylate；prop-2-enyl (2S,4S)-4-benzyl-2-tert-butyl-5-oxo-1,3-oxazolidine-3-carboxylate
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: JMKRTAAWSPXIIZ-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-benzyl-(2S)-tert-butyl-5-oxooxazolidine-3-carboxylic acid allyl ester 在 盐酸 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 7.0h， 生成 (S)-3-methyl-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-allyl ester 3-methyl ester
  参考文献：
  名称：

  Pictet-Spengler环化方法用于构建非蛋白四氢异喹啉季铵盐

  摘要：

  描述了从苯丙氨酸到四氢异喹啉季氨基酸的简单的高度立体选择性的途径。 非对映选择性-氨基酸-苯丙氨酸-四氢异喹啉-氧化-对映体纯

  DOI：

  10.1055/s-0031-1289901
• 作为产物：
  描述：

  L-苯丙氨酸 在 三氟化硼乙醚 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 193.0h， 生成 (4S)-benzyl-(2S)-tert-butyl-5-oxooxazolidine-3-carboxylic acid allyl ester
  参考文献：
  名称：

  Pictet-Spengler环化方法用于构建非蛋白四氢异喹啉季铵盐

  摘要：

  描述了从苯丙氨酸到四氢异喹啉季氨基酸的简单的高度立体选择性的途径。 非对映选择性-氨基酸-苯丙氨酸-四氢异喹啉-氧化-对映体纯

  DOI：

  10.1055/s-0031-1289901

文献信息

• Enantioretentive alkylation of oxazolidinone aluminum enolates with epoxides: Preparation of uncoded homoserine analogs
  作者：Amos B. Smith、Alexander Pasternak、Akihisa Yokoyama、Ralph Hirschmann

  DOI：10.1016/0040-4039(94)88404-8

  日期：1994.11

  The alkylation of Karady/Seebach oxazolidinone enolates with epoxides, promoted by 2.1 equivalents of diethylaluminum chloride, furnishes ring-opened adducts in moderate-to-good yields with high diastereoselectivity. The method provides an effective approach to uncoded homoserine analogs and expands the utility of readily available oxazolidinones in asymmetric synthesis.

  Karady / Seebach恶唑烷酮烯醇烯酸酯与环氧化物的烷基化，由2.1当量的二乙基氯化铝促进，以中等至良好的收率和高非对映选择性提供开环加合物。该方法为未编码的高丝氨酸类似物提供了有效的方法，并扩大了不对称合成中容易获得的恶唑烷酮的实用性。
• Novel bicyclic cyanoheterocycles, process for their preparation and their use as medicaments
  申请人：Wagner Holger

  公开号：US20050059716A1

  公开（公告）日：2005-03-17

  The invention relates to compounds of the formula I in which the radicals have the stated meanings, their stereoisomeric forms and their physiologically tolerated salts and process for their preparation. The compounds are suitable for the treatment of metabohlic disorders such as type 2 diabetes.

  本发明涉及公式I的化合物，其中基团具有所述的含义，它们的立体异构体形式和其生理上可耐受的盐以及它们的制备过程。这些化合物适用于治疗代谢性疾病，如2型糖尿病。
• Bicyclic cyanoheterocycles, process for their preparation and their use as medicaments
  申请人：Sanofi-Aventis Deutschland GmbH

  公开号：US07008957B2

  公开（公告）日：2006-03-07

  The invention relates to compounds of the formula I in which the radicals have the stated meanings, their stereoisomeric forms and their physiologically tolerated salts and process for their preparation. The compounds are suitable for the treatment of metabohlic disorders such as type 2 diabetes.

  本发明涉及式I化合物，其中基团具有所述含义，它们的立体异构体形式和其生理上耐受的盐以及制备它们的过程。这些化合物适用于治疗代谢性疾病，如2型糖尿病。
• Pyrrolinone-Based HIV Protease Inhibitors. Design, Synthesis, and Antiviral Activity: Evidence for Improved Transport
  作者：Amos B Smith、Ralph Hirschmann、Alexander Pasternak、Mark C. Guzman、Akihisa Yokoyama、Paul A. Sprengeler、Paul L. Darke、Emilio A. Emini、William A. Schleif

  DOI：10.1021/ja00150a011

  日期：1995.11

  Pyrrolinone-based peptidomimetics, the first mimics of beta-strands, are potent inhibitors of HIV-1 protease. Importantly, the bis(pyrrolinones) described herein proved to be more active in cellular antiviral assays compared with an analogous peptide-derived inhibitor even though they are less effective in inhibiting the isolated protease. These results suggest that pyrrolinone inhibitors offer better transport properties than the corresponding peptide-based peptidomimetics; we attribute this effect to decreased solvation of the mimetics. Structure-activity relationships for the pyrrolinones correlate well with those reported for related peptides, consistent with similar modes of binding.
• An unusual functional group interaction and its potential to reproduce steric and electrostatic features of the transition states of peptidolysis
  作者：Arnaud Gautier、Delphine Pitrat、Jens Hasserodt

  DOI：10.1016/j.bmc.2006.01.031

  日期：2006.6

  The donor-acceptor interaction between a tertiary amine and an aldehyde, first observed among a select class of alkaloids, was deliberately established in a peptidomimetic (1a-c) to mimic features of the two principal transition states of peptide hydrolysis. Compounds la-c show preferential adoption in methanol and water of a 'folded' conformation displaying the interaction. Proportions of the folded form in MeOH range from 45% to 70% and can reach 84% in buffer. Significantly, three tendencies for the folded/unfolded equilibrium are observed: increasing solubility and polarity of the medium and decreasing temperature results in a higher extent of folding. In the absence of any parameter set available for this weak bond, no modeling studies were conducted to aid in the design of 1a-c. The successful straightforward synthesis of 1 and its folding and inhibition results with HIV-1 peptidase using FRET technology encourage studies to further preorganize candidate molecules and to screen the structure space by modeling and parallel combinatorial chemistry. (c) 2006 Elsevier Ltd. All rights reserved.