(2'R,3'R,4R,5S)-(E)-3-(2',4'-dimethyl-3'-hydroxy-4'-hexenoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one | 694440-05-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (2'R,3'R,4R,5S)-(E)-3-(2',4'-dimethyl-3'-hydroxy-4'-hexenoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one
• 英文别名: (4R,5S,2'R,3'R,4'E)-3-(2',4'-dimethyl-3'-hydroxy-1'-oxo-4'-hexenyl)-4-methyl-5-phenyl-2-oxazolidinone；(4R,5S)-3-[(2R,3R,4E)-3-hydroxy-2,4-dimethyl-4-hexenoyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one；(4R,5S)-3-[(E,2R,3R)-3-hydroxy-2,4-dimethylhex-4-enoyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one
• CAS: 694440-05-6
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: UXOPVZQGQPPOIX-VMURMBNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2'R,3'R,4R,5S)-(E)-3-(2',4'-dimethyl-3'-hydroxy-4'-hexenoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one 在 2,6-二甲基吡啶 、 三甲基铝 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 11.17h， 生成 tert-Butyl-[(E)-(R)-2-methyl-1-((S)-1-methyl-prop-2-ynyl)-but-2-enyloxy]-diphenyl-silane
  参考文献：
  名称：

  Mechanistic Studies on the O-Directed Free-Radical Hydrostannation of Disubstituted Acetylenes with Ph₃SnH and Et₃B and on the Iodination of Allylically Oxygenated α-Triphenylstannylalkenes

  摘要：

  The free-radical hydrostannation of 1 with Ph3SnH and catalytic Et3B in PhMe has been mechanistically probed. At high Ph3SnH concentrations, the O-directed hydrostannation pathway dominates, and 2 is formed with good selectivity (ca. 11.1:1). Substantially lower stannane/substrate concentrations increase the amount of tandem 5-exo-trig cyclization product 3 that is observed.

  DOI：

  10.1021/ol051937d
• 作为产物：
  描述：

  反式-2-甲基-2-丁烯醛 、 (4R,5S)-3-丙酰基-4-甲基-5-苯基-2-噁唑烷酮 在 三氟甲磺酸二丁硼 、 三乙胺 、 双氧水 作用下， 以 二氯甲烷 、 甲醇 、 phosphate buffer 为溶剂， 反应 4.0h， 以88%的产率得到(2'R,3'R,4R,5S)-(E)-3-(2',4'-dimethyl-3'-hydroxy-4'-hexenoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  立体合成抗生素制霉菌素A1的非天然对映体的C21-C38片段。

  摘要：

  制霉菌素A（1）的非天然对映异构体1的C（21）-C（38）片段全反式41是从N-丙酰恶唑烷酮9制备的。衍生的醛醇加合物ent-8（ee> 96％）分两步用（thexyl）BH（2）硼氢化。氧化后处理，并用酸提供的δ-内酯4进行处理。它包含目标分子的完整立体四聚体。在另外四个步骤之后获得了α，β-不饱和酯28。它应该是多种多元醇，多烯大环内酯的多烯部分的前体。说明从28和DIBAL获得的α，β-不饱和醛29在四个步骤中扩展了10个C原子，得到C（21）-C（38）段41。后一组转化包括区域选择性和立体选择性克莱森重新排列32-> 35。

  DOI：

  10.1002/chem.200305540

文献信息

• CYCLIC PEPTIDE ANALOGS AND CONJUGATES THEREOF
  申请人：Sirenas LLC

  公开号：US20170015710A1

  公开（公告）日：2017-01-19

  Provided are cyclic peptide analogs, conjugates comprising such compounds, and pharmaceutical compositions comprising such compounds and conjugates, and methods of treating cancer with such compounds and conjugates.

  提供了环肽类似物，包括这些化合物的共轭物，以及包含这些化合物和共轭物的药物组合物，以及使用这些化合物和共轭物治疗癌症的方法。
• Stereocontrolled Synthesis of the C21–C38 Fragment of the Unnatural Enantiomer of the Antibiotic Nystatin A1
  作者：Thilo Berkenbusch、Reinhard Brückner

  DOI：10.1002/chem.200305540

  日期：2004.3.19

  The C(21)-C(38) fragment all-trans-41 of the unnatural enantiomer 1 of nystatin A(1) was prepared starting from the N-propionyl oxazolidinone 9. Aldol adduct ent-8 (ee > 96 %) derived in two steps was hydroborated with (thexyl)BH(2). Oxidative work-up and treatment with acid furnished delta-lactone 4. It contains the complete stereotetrade of the target molecule. The alpha,beta-unsaturated ester 28

  制霉菌素A（1）的非天然对映异构体1的C（21）-C（38）片段全反式41是从N-丙酰恶唑烷酮9制备的。衍生的醛醇加合物ent-8（ee> 96％）分两步用（thexyl）BH（2）硼氢化。氧化后处理，并用酸提供的δ-内酯4进行处理。它包含目标分子的完整立体四聚体。在另外四个步骤之后获得了α，β-不饱和酯28。它应该是多种多元醇，多烯大环内酯的多烯部分的前体。说明从28和DIBAL获得的α，β-不饱和醛29在四个步骤中扩展了10个C原子，得到C（21）-C（38）段41。后一组转化包括区域选择性和立体选择性克莱森重新排列32-> 35。
• Cyclic peptide analogs and conjugates thereof
  申请人：Sirenas LLC

  公开号：US10472395B2

  公开（公告）日：2019-11-12

  Provided are cyclic peptide analogs, conjugates comprising such compounds, and pharmaceutical compositions comprising such compounds and conjugates, and methods of treating cancer with such compounds and conjugates.

  本文提供了环肽类似物、包含此类化合物的共轭物、包含此类化合物和共轭物的药物组合物，以及用此类化合物和共轭物治疗癌症的方法。
• Synthetic studies on the azinothricin family of antibiotics. 2. Asymmetric synthesis of the C(28)–C(47) subunit of A83586C
  作者：Karl J. Hale、Gurpreet S. Bhatia、S.Andrew Peak、Soraya Manaviazar

  DOI：10.1016/s0040-4039(00)73993-1

  日期：1993.8

  An asymmetric synthesis of the C(28)-C(47) segment of the antitumour antibiotic A83586C is described.
• Synthesis of the Aliphatic Depside (+)-Bourgeanic Acid
  作者：James D. White、Alan T. Johnson

  DOI：10.1021/jo00091a022

  日期：1994.6

  The lichen metabolite (+)-bourgeanic acid (1) was synthesized in 12 steps and 3.4% overall yield from (R)-2-methyl-1-iodobutane (53) by a sequence which confirmed that this aliphatic depside is the self-esterification product of (2S,3S,4R,6R)-2,4,6-trimethyl-3-hydroxyoctanoic acid. Alkylation of the enolate of (S)-N-propionylprolinol (48) with 53 gave the amide 60 which was transformed to (2R,4R)-2,4-dimethylhexanal (4). The latter was reacted with the crotylboronate 68, prepared from (S,S)-(-)-diisopropyltartrate, to afford (3R,4S,5R,7R)-3,5,7-trimethyl-1-nonen-4-ol (65) as the major diastereomer. Protection followed by ozonolysis and oxidation furnished (-)-hemibourgeanic acid (2). The beta-lactone 73 derived from 2 was used to acylate 65, and the resulting ester 74 was subjected to oxidative ozonolysis to yield (+)-1.