(R)-2-[(1R,2S)-1-(3-Methyl-butyryloxy)-2-triethylsilanyloxy-propyl]-hexanoic acid benzyl ester | 764651-36-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-[(1R,2S)-1-(3-Methyl-butyryloxy)-2-triethylsilanyloxy-propyl]-hexanoic acid benzyl ester
• 英文别名: benzyl (2R)-2-[(1R,2S)-1-(3-methylbutanoyloxy)-2-triethylsilyloxypropyl]hexanoate
• CAS: 764651-36-7
• 化学式: C₂₇H₄₆O₅Si
• 分子量: 478.745
• InChiKey: HJYWIRJHTDPPAI-FBILRYNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  33
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-2-[(1R,2S)-1-(3-Methyl-butyryloxy)-2-triethylsilanyloxy-propyl]-hexanoic acid benzyl ester 在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以98%的产率得到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：

  1-[(4R)-4-phenyl-2-sulfanylidene-1,3-oxazolidin-3-yl]hexan-1-one 在 吡啶 、 4-二甲氨基吡啶 、 四甲基乙二胺 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 64.5h， 生成 (R)-2-[(1R,2S)-1-(3-Methyl-butyryloxy)-2-triethylsilanyloxy-propyl]-hexanoic acid benzyl 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

• Removal of Thiazolidinethione Auxiliaries with Benzyl Alcohol Mediated by DMAP
  作者：Yikang Wu、Ya-Ping Sun、Yong-Qing Yang、Qi Hu、Qi Zhang

  DOI：10.1021/jo049204e

  日期：2004.9.1

  In the presence of DMAP, a range of N-acylthiazaolidinethiones carrying different substituents were smoothly converted into the corresponding benzyl esters.

  在DMAP的存在下，将一系列带有不同取代基的N-酰基噻唑烷硫酮平稳地转化为相应的苄基酯。
• 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.