(3RS,5S,3'EZ)-3-(4'-iodo-3'-butenyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one | 210160-15-9

• 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'EZ)-3-(4'-iodo-3'-butenyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one
• CAS: 210160-15-9
• 化学式: C₁₅H₁₇IO₂S
• 分子量: 388.269
• InChiKey: HCUOTVPLACORAM-SFVWDYPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,5R,1'R,4'S,5'S,8'S,1"R)-2-(5',8'-epoxy-4'-hydroxy-1'-methoxymethoxy-10'-undecynyl)-5-(1"-methoxymethoxytridecyl)tetrahydrofuran 、 (3RS,5S,3'EZ)-3-(4'-iodo-3'-butenyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one 在 四(三苯基膦)钯 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.0h， 以60%的产率得到(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 chromium dichloride 、 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 (3RS,5S,3'EZ)-3-(4'-iodo-3'-butenyl)-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