(3RS,5S)-3-(2'-formylethyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one | 210160-17-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (3RS,5S)-3-(2'-formylethyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one
• CAS: 210160-17-1
• 化学式: C₁₄H₁₆O₃S
• 分子量: 264.345
• InChiKey: OSACLKKVLVUJJY-ZSOXZCCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3RS,5S)-3-(2'-formylethyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one 在 四(三苯基膦)钯 chromium dichloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 10.0h， 生成 (3RS,5S,8'S,11'S,12'S,15'R,16'R,19'R,20'R,EZ)-3-[8',11':16',19'-diepoxy-12'-hydroxy-15',20'-bis(methoxymethoxy)-3'-dotriaconten-5'-ynyl]-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one
  参考文献：
  名称：

  Total synthesis of (+)-4-deoxygigantecin

  摘要：

  A total synthesis of a non-adjacent bis-tetrahydrofuranyl annonaceous acetogenin, (+)-4-deoxygigantecin (1) is described. Mono-tetrahydrofuran building block (10), of which the synthesis from (-)-muricatacin (8) had been described in an earlier report, was converted to bis-MOM ether (9) through two-step reactions. Transformation of this compound into non-adjacent bis-tetrahydrofuran unit (5) was carried out by a twelve-step sequence of reactions. Pd(0)-catalyzed cross coupling reaction between 5 and iodinated butenolide (7), which had been prepared from(S)-(-)-ethyl lactate, led to enyne (4). Finally, this compound was converted to (+) -4-deoxygigantecin (1) by two steps. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00285-3
• 作为产物：
  描述：

  (3RS,5S)-3-[3'-(tetrahydro-2-pyranyloxy)propyl]-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one 在 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (3RS,5S)-3-(2'-formylethyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one
  参考文献：
  名称：

  Total synthesis of (+)-4-deoxygigantecin

  摘要：

  A total synthesis of a non-adjacent bis-tetrahydrofuranyl annonaceous acetogenin, (+)-4-deoxygigantecin (1) is described. Mono-tetrahydrofuran building block (10), of which the synthesis from (-)-muricatacin (8) had been described in an earlier report, was converted to bis-MOM ether (9) through two-step reactions. Transformation of this compound into non-adjacent bis-tetrahydrofuran unit (5) was carried out by a twelve-step sequence of reactions. Pd(0)-catalyzed cross coupling reaction between 5 and iodinated butenolide (7), which had been prepared from(S)-(-)-ethyl lactate, led to enyne (4). Finally, this compound was converted to (+) -4-deoxygigantecin (1) by two steps. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00285-3