3-[3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-1-trimethylsilyl-propyne | 875439-71-7

• 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: 3-[3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-1-trimethylsilyl-propyne
• CAS: 875439-71-7
• 化学式: C₃₃H₄₃NO₃Si₂
• 分子量: 557.88
• InChiKey: ZYWLSLKPLHOQPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-[3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-1-trimethylsilyl-propyne 在 palladium diacetate 吡啶 、 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 二氯二茂锆 、 2-甲基-2-丁烯 、 草酰氯 、 四丁基氟化铵 、 四丁基溴化铵 、 碘 、 caesium carbonate 、 氟化氢吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 100.83h， 生成 (4E,11E,13E)-(3S,6S,7S,10R)-3,7-Dihydroxy-10-methoxy-4,6,14-trimethyl-9-oxo-15-[3-(2-trimethylsilanyl-ethoxycarbonylamino)-5-(2-trimethylsilanyl-ethoxycarbonyloxy)-phenyl]-pentadeca-4,11,13-trienethioic acid S-(2-acetylamino-ethyl) ester
  参考文献：
  名称：

  Synthesis of the N-Acetylcysteamine Thioester of seco-Proansamitocin

  摘要：

  The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated alkynylation of a benzyl bromide followed by carboalumination. The key step is a Heck reaction between two terminal alkenes for merging the two major fragments.

  DOI：

  10.1021/ol052588q
• 作为产物：
  描述：

  3-tert-butoxycarbonylamino-5-(tert-butyl-diphenylsilanyloxy)-benzyl bromide 、 三(2-(三甲基甲硅烷基)乙炔基)铟 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以96%的产率得到3-[3-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-1-trimethylsilyl-propyne
  参考文献：
  名称：

  Synthesis of the N-Acetylcysteamine Thioester of seco-Proansamitocin

  摘要：

  The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated alkynylation of a benzyl bromide followed by carboalumination. The key step is a Heck reaction between two terminal alkenes for merging the two major fragments.

  DOI：

  10.1021/ol052588q

文献信息

• Chemoenzymatic Approaches toward Dechloroansamitocin P-3
  作者：Axel Meyer、Marco Brünjes、Florian Taft、Thomas Frenzel、Florenz Sasse、Andreas Kirschning

  DOI：10.1021/ol0702270

  日期：2007.4.1

  The enantioselective total synthesis of proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin P-3, is described which bears a diene-ene RCM as the key macrocyclization step. Feeding of proansamitocin to an AHBA block mutant Actinosynnema pretiosum (HGF073) yielded ansamitocin P-3 as well as dechloroansamitocin P-3, the latter also being formed upon fermentation in the presence of 3-amino-5-methoxybenzoic acid.