[(2S,3R,4R)-4-[(4R)-4-phenyl-2-sulfanylidene-1,3-oxazolidine-3-carbonyl]-2-triethylsilyloxyoctan-3-yl] 3-methylbutanoate | 896434-07-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(2S,3R,4R)-4-[(4R)-4-phenyl-2-sulfanylidene-1,3-oxazolidine-3-carbonyl]-2-triethylsilyloxyoctan-3-yl] 3-methylbutanoate
• CAS: 896434-07-4
• 化学式: C₂₉H₄₇NO₅SSi
• 分子量: 549.847
• InChiKey: DCIFPZDKOXDNDG-YRMGXDARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.05
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  97.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4R)-4-[(4R)-4-phenyl-2-sulfanylidene-1,3-oxazolidine-3-carbonyl]-2-triethylsilyloxyoctan-3-yl] 3-methylbutanoate 在 4-二甲氨基吡啶 、 sodium periodate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 49.5h， 生成 benzyl (2R)-2-[(1R,2S)-2-hydroxy-1-(3-methylbutanoyloxy)propyl]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
• 作为产物：
  描述：

  (R)-4-苯基-1,3-噁唑啉-2-硫酮 在 吡啶 、 4-二甲氨基吡啶 、 四甲基乙二胺 、 四氯化钛 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 34.5h， 生成 [(2S,3R,4R)-4-[(4R)-4-phenyl-2-sulfanylidene-1,3-oxazolidine-3-carbonyl]-2-triethylsilyloxyoctan-3-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

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.