tert-Butyl-[(3E,5E,9Z,11E)-(2R,8R)-1,10-diethyl-12-((2R,6R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl)-2,4,8-trimethyl-dodeca-3,5,9,11-tetraenyloxy]-dimethyl-silane | 372937-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: tert-Butyl-[(3E,5E,9Z,11E)-(2R,8R)-1,10-diethyl-12-((2R,6R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl)-2,4,8-trimethyl-dodeca-3,5,9,11-tetraenyloxy]-dimethyl-silane
• 英文别名: tert-butyl-[(4R,5E,7E,10R,11Z,13E)-12-ethyl-4,6,10-trimethyl-14-[(2R,6R)-6-propan-2-yloxy-3,6-dihydro-2H-pyran-2-yl]tetradeca-5,7,11,13-tetraen-3-yl]oxy-dimethylsilane
• CAS: 372937-52-5
• 化学式: C₃₃H₅₈O₃Si
• 分子量: 530.907
• InChiKey: BVYKSWLTKGTREL-MYSAQWKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.94
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-Butyl-[(3E,5E,9Z,11E)-(2R,8R)-1,10-diethyl-12-((2R,6R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl)-2,4,8-trimethyl-dodeca-3,5,9,11-tetraenyloxy]-dimethyl-silane 在 草酰氯 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (4R,5E,7E,10R,11Z,13E)-12-ethyl-4,6,10-trimethyl-14-[(2R,6R)-6-propan-2-yloxy-3,6-dihydro-2H-pyran-2-yl]tetradeca-5,7,11,13-tetraen-3-one
  参考文献：
  名称：

  Total Synthesis of (−)-Callystatin A

  摘要：

  [GRAPHICS]The enantioselective synthesis of callystatin A is described. The pivotal step in the synthesis is the stereoselective aldol reaction that generates the beta -hydroxy ketone moiety. Utilizing the allylic strain within the ethyl ketone precursor, we were able to generate the all-syn configuration of callystatin A. For the construction of the two diene moieties, both a Heck coupling and a Wittig reaction were employed.

  DOI：

  10.1021/ol016365l
• 作为产物：
  描述：

  tert-Butyl-((R)-1-ethyl-2-methyl-pent-3-ynyloxy)-dimethyl-silane 在 palladium diacetate Schwartz's reagent 、 18-冠醚-6 、 四溴化碳 、 potassium tert-butylate 、 silver(I) acetate 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 10.75h， 生成 tert-Butyl-[(3E,5E,9Z,11E)-(2R,8R)-1,10-diethyl-12-((2R,6R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl)-2,4,8-trimethyl-dodeca-3,5,9,11-tetraenyloxy]-dimethyl-silane
  参考文献：
  名称：

  Total Synthesis of (−)-Callystatin A

  摘要：

  [GRAPHICS]The enantioselective synthesis of callystatin A is described. The pivotal step in the synthesis is the stereoselective aldol reaction that generates the beta -hydroxy ketone moiety. Utilizing the allylic strain within the ethyl ketone precursor, we were able to generate the all-syn configuration of callystatin A. For the construction of the two diene moieties, both a Heck coupling and a Wittig reaction were employed.

  DOI：

  10.1021/ol016365l

文献信息

• Total Synthesis of (−)-Callystatin A
  作者：Markus Kalesse、Monika Quitschalle、Chary P. Khandavalli、Aamer Saeed

  DOI：10.1021/ol016365l

  日期：2001.10.1

  [GRAPHICS]The enantioselective synthesis of callystatin A is described. The pivotal step in the synthesis is the stereoselective aldol reaction that generates the beta -hydroxy ketone moiety. Utilizing the allylic strain within the ethyl ketone precursor, we were able to generate the all-syn configuration of callystatin A. For the construction of the two diene moieties, both a Heck coupling and a Wittig reaction were employed.