benzyl (2R)-2-[(1R,2S)-1-(3-methylbutanoyloxy)-2-[(2S,3R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxybutanoyl]oxypropyl]hexanoate | 896434-09-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl (2R)-2-[(1R,2S)-1-(3-methylbutanoyloxy)-2-[(2S,3R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxybutanoyl]oxypropyl]hexanoate
• CAS: 896434-09-6
• 化学式: C₃₇H₅₃NO₉
• 分子量: 655.829
• InChiKey: FCPYICVUJVYIOI-VKTAPIASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  47
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzyl (2R)-2-[(1R,2S)-1-(3-methylbutanoyloxy)-2-[(2S,3R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxybutanoyl]oxypropyl]hexanoate 在 palladium dihydroxide 4-二甲氨基吡啶 、 4 A molecular sieve 、 2-甲基-6-硝基苯甲酸酐 、 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 20.0~40.0 ℃ 、3.04 MPa 条件下， 反应 24.0h， 生成 3-Methyl-butyric acid (2R,3S,6S,7R,8R)-3-tert-butoxycarbonylamino-8-butyl-2,6-dimethyl-4,9-dioxo-[1,5]dioxonan-7-yl ester
  参考文献：
  名称：

  An Expeditious Enantioselective Synthesis of Antimycin A_3b

  摘要：

  A straightforward enantioselective route to (+)-antimycin A(3b) is presented, which used a TiCl4-mediated asymmetric aldolization to construct C-7/C-8 and BnOH/DMAP to remove the chiral auxiliary with concurrent protection of the carboxylic group, respectively. Closing the dilactone ring was achieved in 62% yield (previously 0.8%, 13.4%, or 20%) in the presence of the C-8 ester functionality. The overall yield (34.5%) was significantly higher than that (0.019-3.6%) of the earlier routes.

  DOI：

  10.1021/jo0604890
• 作为产物：
  描述：

  (R)-2-[(1R,2S)-1-(3-Methyl-butyryloxy)-2-triethylsilanyloxy-propyl]-hexanoic acid benzyl ester 在 4-二甲氨基吡啶 、 sodium periodate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 29.0h， 生成 benzyl (2R)-2-[(1R,2S)-1-(3-methylbutanoyloxy)-2-[(2S,3R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxybutanoyl]oxypropyl]hexanoate
  参考文献：
  名称：

  An Expeditious Enantioselective Synthesis of Antimycin A_3b

  摘要：

  A straightforward enantioselective route to (+)-antimycin A(3b) is presented, which used a TiCl4-mediated asymmetric aldolization to construct C-7/C-8 and BnOH/DMAP to remove the chiral auxiliary with concurrent protection of the carboxylic group, respectively. Closing the dilactone ring was achieved in 62% yield (previously 0.8%, 13.4%, or 20%) in the presence of the C-8 ester functionality. The overall yield (34.5%) was significantly higher than that (0.019-3.6%) of the earlier routes.

  DOI：

  10.1021/jo0604890