Acetic acid (E)-(S)-1-((2S,3R)-3-allyl-oxiranylmethyl)-2-methyl-3-(2-methyl-thiazol-4-yl)-allyl ester | 197233-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Acetic acid (E)-(S)-1-((2S,3R)-3-allyl-oxiranylmethyl)-2-methyl-3-(2-methyl-thiazol-4-yl)-allyl ester
• CAS: 197233-15-1
• 化学式: C₁₆H₂₁NO₃S
• 分子量: 307.414
• InChiKey: YKOWNKTZBUQLNH-KRENCNMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.72
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (E)-(S)-1-((2S,3R)-3-allyl-oxiranylmethyl)-2-methyl-3-(2-methyl-thiazol-4-yl)-allyl ester 、 (3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,4,6-tetramethyl-3-triphenylsilanyloxy-oct-7-enal 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 、
  参考文献：
  名称：

  Total Syntheses of Epothilones A and B

  摘要：

  Convergent, stereocontrolled total syntheses of the microtubule-stabilizing macrolides epothilones A (2) and B (3) have been achieved. Four distinct ring-forming strategies were pursued (see Scheme 1). Of these four, three were reduced to practice. In one approach, the action of a base on a substance possessing an acetate ester and a nonenolizable aldehyde brought about a remarkably effective macroaldolization see (89 --> 90 + 91; 99 --> 100 + 101), simultaneously creating the C2-C3 bond and the hydroxyl-bearing stereocenter at C-3. Alternatively, the 16-membered macrolide of the epothilones could be fashioned through a C12-C13 ring-closing olefin metathesis (e.g. see 111 --> 90 + 117; 122 --> 105 + 123) and through macrolactonization of the appropriate hydroxy acid (e.g. see 88 --> 93). The application of a stereospecific B-alkyl Suzuki coupling strategy permitted the establishment of a cis C12-C13 olefin, thus setting the stage for an eventual site-and diastereoselective epoxidation reaction (see 96 --> 2; 106 --> 3). The development of a novel cyclopropane solvolysis strategy for incorporating the geminal methyl groups of the epothilones (see 39 --> 40 --> 41), and the use of Lewis acid catalyzed diene-aldehyde cyclocondensation (LACDAC) (see 35 + 36 --> 37) and asymmetric allylation (see 10 --> 76) methodology are also noteworthy.

  DOI：

  10.1021/ja971946k
• 作为产物：
  描述：

  [(2S,4S)-2-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-3,4-dihydro-2H-pyran-4-yl] acetate 在 4-二甲氨基吡啶 、 sodium periodate 、 二甲基二环氧乙烷 、 四氯化锡 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 Acetic acid (E)-(S)-1-((2S,3R)-3-allyl-oxiranylmethyl)-2-methyl-3-(2-methyl-thiazol-4-yl)-allyl ester
  参考文献：
  名称：

  Total Syntheses of Epothilones A and B

  摘要：

  Convergent, stereocontrolled total syntheses of the microtubule-stabilizing macrolides epothilones A (2) and B (3) have been achieved. Four distinct ring-forming strategies were pursued (see Scheme 1). Of these four, three were reduced to practice. In one approach, the action of a base on a substance possessing an acetate ester and a nonenolizable aldehyde brought about a remarkably effective macroaldolization see (89 --> 90 + 91; 99 --> 100 + 101), simultaneously creating the C2-C3 bond and the hydroxyl-bearing stereocenter at C-3. Alternatively, the 16-membered macrolide of the epothilones could be fashioned through a C12-C13 ring-closing olefin metathesis (e.g. see 111 --> 90 + 117; 122 --> 105 + 123) and through macrolactonization of the appropriate hydroxy acid (e.g. see 88 --> 93). The application of a stereospecific B-alkyl Suzuki coupling strategy permitted the establishment of a cis C12-C13 olefin, thus setting the stage for an eventual site-and diastereoselective epoxidation reaction (see 96 --> 2; 106 --> 3). The development of a novel cyclopropane solvolysis strategy for incorporating the geminal methyl groups of the epothilones (see 39 --> 40 --> 41), and the use of Lewis acid catalyzed diene-aldehyde cyclocondensation (LACDAC) (see 35 + 36 --> 37) and asymmetric allylation (see 10 --> 76) methodology are also noteworthy.

  DOI：

  10.1021/ja971946k