prop-2-enyl (2R,4S)-4-benzyl-2-tert-butyl-4-[(2S,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutyl]-5-oxo-1,3-oxazolidine-3-carboxylate | 160978-16-5

• 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: prop-2-enyl (2R,4S)-4-benzyl-2-tert-butyl-4-[(2S,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutyl]-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 160978-16-5
• 化学式: C₃₃H₄₄N₂O₇
• 分子量: 580.722
• InChiKey: BPRIHMWEFNZRRE-IULAASEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  prop-2-enyl (2R,4S)-4-benzyl-2-tert-butyl-4-[(2S,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutyl]-5-oxo-1,3-oxazolidine-3-carboxylate 在 盐酸 、 sodium hydroxide 、 四(三苯基膦)钯 、 jones reagent 、 氨 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 5,5-二甲基-1,3-环己二酮 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 196.17h， 生成 methyl (2R)-2-[(5S)-5-[(5S)-5-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutyl]-5-benzyl-4-oxo-1H-pyrrol-3-yl]-5-(2-methylpropyl)-4-oxo-1H-pyrrol-3-yl]-3-phenylpropanoate
  参考文献：
  名称：

  Pyrrolinone-Based HIV Protease Inhibitors. Design, Synthesis, and Antiviral Activity: Evidence for Improved Transport

  摘要：

  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.

  DOI：

  10.1021/ja00150a011
• 作为产物：
  描述：

  (1S)-1-(2R)-环氧乙基-2-苯乙基氨基甲酸叔丁酯 、 (2R,4R)-4-Benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester 在 氯化二乙基铝 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到prop-2-enyl (2R,4S)-4-benzyl-2-tert-butyl-4-[(2S,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutyl]-5-oxo-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  恶唑烷酮烯醇铝与环氧化物的对映体烷基化：未编码的高丝氨酸类似物的制备

  摘要：

  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。

  DOI：

  10.1016/0040-4039(94)88404-8

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。
• 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.