(4S)-3-<(2'S,3'R)-3'-hydroxy-2'-methylpentanoyl>-4-isopropyl-1,3-oxazolidin-2-one | 88636-00-4

• 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: (4S)-3-<(2'S,3'R)-3'-hydroxy-2'-methylpentanoyl>-4-isopropyl-1,3-oxazolidin-2-one
• 英文别名: (2'S,3'R,4S)-3-(3'-Hydroxy-2'-methyl-1'-oxopentyl)-4-(methylethyl)-2-oxazolidinone；(4S)-3-[(2S,3R)-3-hydroxy-2-methylpentanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 88636-00-4
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: HYPZLCYGHIXOHV-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (4S)-3-<(2'S,3'R)-3'-hydroxy-2'-methylpentanoyl>-4-isopropyl-1,3-oxazolidin-2-one 在 lithium hydroxide 、 双氧水 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 为溶剂， 反应 16.5h， 生成 methyl ester of/the/ (+)(S)-methylpropylacetic acid
  参考文献：
  名称：

  Structural Elucidation of Twelve Novel Esters Composed of Five Fatty Acids and Three New Branched Alcohols Together with Four Monoterpenoids from Sancassania shanghaiensis (Acari: Acaridae)

  摘要：

  GC/MS分析在Sancassania shanghaiensis的抱粉腺成分中检测到总共12种新型酯和4种单萜（玫瑰呋喃、（2R,3R）-环氧橙花醇以及α-和β-刺檗二醇）。经过水解后的酸性部分由5种常见脂肪酸（棕榈酸、硬脂酸、油酸、亚油酸和花生酸）组成，而醇性部分则主要由两种成分（带有支链甲基的C6和C8醇）组成，同时含有微量的C9醇。通过比较其3,5-二硝基苯甲酸酯的物理化学数据与选择性合成醇的数据，确认这两种主要醇为新型醇[（S）-2-甲基戊醇和（2S,4S）-2,4-二甲基己醇]。根据结构和生物学上的相似性，C9醇被推测为（2S,4S）-2,4-二甲基庚醇。通过GC鉴定，五种化合物分别为五种脂肪酸的（S）-2-甲基戊酯，另外五种成分同样为（2S,4S）-2,4-二甲基己酯。剩下的两种被推测为（2S,4S）-2,4-二甲基庚酯的硬脂酸酯和亚油酸酯。

  DOI：

  10.1271/bbb.65.919
• 作为产物：
  描述：

  (S)-4-异丙基-3-丙酰基-2-恶唑烷酮 在 Ra-Ni 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (4S)-3-<(2'S,3'R)-3'-hydroxy-2'-methylpentanoyl>-4-isopropyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Acyclic stereoselection. 48. Reversal of stereochemistry in the aldol reactions of a chiral boron enolate

  摘要：

  DOI：

  10.1021/jo00288a029

文献信息

• Toward the total synthesis of hygrolidin: Stereocontrolled construction of the C1–C17 seco-acid fragment and the C18–C25 masked hemiacetal subunit
  作者：Kazuishi Makino、Ken-ichi Kimura、Noriyuki Nakajima、Shun-ichi Hashimoto、Osamu Yonemitsu

  DOI：10.1016/s0040-4039(96)02132-6

  日期：1996.12

  Toward the first total synthesis of 16-membered macrolide antibiotic hygrolidin, the C1C17 seco-acid fragment and the C18C25 masked hemiacetal subunit as potential precursors have been synthesized in enantiomerically homogeneous forms.

  在第一次全合成16元大环内酯类抗生素潮霉素的过程中，C1omerC17癸二酸片段和C18C25掩盖的半缩醛亚基作为对映体均质形式被合成。
• Asymmetric acylation reactions of chiral imide enolates. The first direct approach to the construction of chiral .beta.-dicarbonyl synthons
  作者：D. A. Evans、M. D. Ennis、T. Le、N. Mandel、G. Mandel

  DOI：10.1021/ja00316a077

  日期：1984.2

  Acylation de 2 propionimides chirales: isopropyl-4 propionyl-3 oxazolidone-2 et methyl-4 phenyl-5 propionyl-3 oxazolidone-2

  酰化 2 propionimides 手性：isopropyl-4 propionyl-3 oxazolidone-2 etmethyl-4 phenyl-5 propionyl-3 oxazolidone-2
• Strategies for Macrolide Synthesis. A Concise Approach to Protected Seco-Acids of Erythronolides A and B
  作者：Stephen F. Martin、Wen-Cherng Lee、Gregory J. Pacofsky、Ricky P. Gist、Thomas A. Mulhern

  DOI：10.1021/ja00090a016

  日期：1994.6

  Concise syntheses of protected derivatives of the seco-acids of erythronolides A and B, 5 and 6, respectively, have been completed wherein the longest linear sequence requires only 13 chemical steps from 5-ethylfuraldehyde (15). The syntheses commenced with the asymmetric aldol condensation of 15 according to the Evans protocol to afford the optically pure syn adduct 16, thereby establishing the critical stereocenters at C(4) and C(5) of the erythromycin backbone. Reductive removal of the chiral auxiliary from 16 gave the diol 17, which was converted to the bicyclic enone 18 by an one-pot process involving sequential oxidation of the furan ring and acid-catalyzed bicycloketalization. Stereoselective elaboration of 18 to the tertiary alcohol 19 was achieved in two steps by sequential treatment with lithium dimethylcuprate and methyllithium in the presence of cerium trichloride. Compound 19 underwent facile acid-catalyzed reorganization to the isomeric ketal 21, which was transformed into 24 by a Swern oxidation and a second asymmetric aldol condensation. However, the necessary refunctionalization of 24 into a ketone that would participate in the requisite aldol reaction to append the C(11)-C(15) segment of the erythronolide backbone could not be induced. On the other hand, transthioketalization of 19 gave the triol 26, which was converted to 28 by the thermodynamically-controlled formation of an acetonide of the 1,2-diol array. Deprotection of the C(9) ketone function followed by Swern oxidation produced the keto aldehyde 31, which underwent chemoselective, Lewis acid-mediated addition of tri-n-butylcrotylstannane to the aldehyde function to furnish a mixture (4:1) of the homoallylic alcohols 32 and 33; the major product 32 comprises the C(1)-C(10) subunit common to the seco-acids of both erythronolides A and B. Diastereoselective aldol condensation of the enolate derived from 32 with 40 gave 42 as the major adduct; oxidative processing of the terminal olefin then delivered the erythronolide B seco-acid derivative 46. The proposed structure of 42 was initially based upon its conversion into the polyol 48, which was identical to that derived from natural erythronolide B (49). Subsequent to this chemical correlation, the X-ray structure of 50, which was prepared from 42, unequivocally verified this assignment. In experiments directed toward the preparation of the seco-acid of erythronolide A, the directed aldol reactions of 32 with the aldehydes 59 and 60 were examined. Although the addition of the enolate of 32 to 59 produced none of the requisite adduct, its reaction with 60 gave a mixture (1:5) of 62 and 64. Stereoselective reduction of the C(9) carbonyl function of 62 followed by oxidative cleavage of the double bond and global deprotection gave the polyol 62, which was identical with the polyol derived from natural erythromycin A (1).
• DANDA, HIDENORI;HANSEN, MARVIN M.;HEATHCOCK, CLAYTON H., J. ORG. CHEM., 55,(1990) N, C. 173-181
  作者：DANDA, HIDENORI、HANSEN, MARVIN M.、HEATHCOCK, CLAYTON H.

  DOI：——

  日期：——
• Acyclic stereoselection. 48. Reversal of stereochemistry in the aldol reactions of a chiral boron enolate
  作者：Hidenori Danda、Marvin M. Hansen、Clayton H. Heathcock

  DOI：10.1021/jo00288a029

  日期：1990.1