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 | 896434-11-0

• 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: 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
• 英文别名: [(2R,3S,6S,7R,8R)-8-butyl-2,6-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4,9-dioxo-1,5-dioxonan-7-yl] 3-methylbutanoate
• CAS: 896434-11-0
• 化学式: C₂₃H₃₉NO₈
• 分子量: 457.565
• InChiKey: LZESBUPKHLYEJC-LHHMMCJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  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 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 9.5h， 以100%的产率得到[(2R,3S,6S,7R,8R)-3-amino-8-butyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] 3-methylbutanoate
  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：

  己酰氯 在 palladium dihydroxide 吡啶 、 4-二甲氨基吡啶 、 sodium periodate 、 四甲基乙二胺 、 4 A molecular sieve 、 2-甲基-6-硝基苯甲酸酐 、 氢气 、 四氯化钛 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， -20.0~40.0 ℃ 、3.04 MPa 条件下， 反应 134.0h， 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

文献信息

• An Expeditious Enantioselective Synthesis of Antimycin A_3b
  作者：Yikang Wu、Yong-Qing Yang

  DOI：10.1021/jo0604890

  日期：2006.5.1

  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.